JP2011524859A - 3-Amino-benzo [D] isothiazole dioxide derivatives and their use as insecticides - Google Patents

Abstract

Formula I below:
[Wherein W is CR ³ ; X is CR ⁴ ; Y is CR ⁵ ; R ¹ and R ⁶ are independently of each other H, C1-C6-alkyl, C2- C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C1-C6-alkyl-C (═O); R ² is H; and R ³ , R ⁴ and R ⁵ are Independently of each other, H, halogen, cyano, nitro, C1-C6-alkyl or C1-C6-haloalkyl; provided that in formula II, R ¹ is H and R ⁶ is as defined above And in Formula I, (a) at least one of R ¹ and R ³ -R ⁶ is other than hydrogen, and (b) R ³ or R ⁴ is in each case R ¹ -R ⁶ When the five remaining groups are hydrogen, it is other than Cl, and (c) (i) R ³ is other than methyl, (ii) R ⁴ is other than Cl, and (iii) R ⁵ is other than Cl. And (iv) when R ⁵ is methoxy, R ³ is not Cl and (i) to (iv) And R ¹ is H, R ⁶ is MeC (= O), and the remaining groups of R ^{2 to} R ⁵ are hydrogen, and / or a salt thereof; and Their use as insecticides.

Description

  The present invention relates to defined 3-amino-1,2-benzisothiazole dioxide derivatives and their salts, their compositions and treated materials, and methods of using such compounds and salts.

  EP 33984, EP 86748, EP 110829, DE 3544436, EP 191734, EP 207891, EP 01319467, JP 02006496, WO 2007057407 and WO 2007113119 are certain 3-amino acids having insecticidal activity. Disclosed are 1,2-benzisothiazole dioxide derivatives.

  It has now been found that certain 3-amino-1,2-benzisothiazole dioxide derivatives have insecticidal properties. Accordingly, in a first aspect, the present invention provides the following formula I or II:

[Wherein W is CR ³ ;
X is CR ⁴ ;
Y is CR ⁵ ;
R ¹ and R ⁶ are independently of each other H, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, R ⁷ C (═O) or R ⁸ HNC. (= O), where C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, R ⁷ C (= O) or R ⁸ HNC (= O) The groups can be unsubstituted or carry one or more halogen atoms and / or independently of each other cyano, nitro, amino, OH, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkoxy, C1-C6-haloalkylthio, (C1- C6-alkoxy) carbonyl, (C1-C6-alkyl) amino, di- (C1-C6-alkyl) amino, C3-C8-cycloalkyl, C1-C6-alkylcarbonyloxy, arylcarbonyloxy 1, 2 or 3 groups, each selected from the group consisting of xyl and aryl, can be carried, wherein said aryl group is unsubstituted or can carry one or more halogen atoms. Can be and / or independently of one another, selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, cyano and nitro, 1, 2 or Can carry three substituents;

R ² is H;
R ³ , R ⁴ and R ⁵ are independently of each other H, halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, C2-C6-alkenyl, N- combined 4-7 membered N-containing heterocycle, C2-C6- ^{alkynyl, R 9 C (= O)} , it is a OD or aryl; where D is C1-C6- alkyl, C2-C6- alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, benzyl or aryl; the 4-7 membered heterocycle, in addition to the bonded N atom, is independently of each other C (= O), O 1, 2 or 3 heteroatoms and / or heteroatoms as ring members selected from S, N and can be substituted or unsubstituted or halogen, C1-C6- (halo ) May be substituted by 1 or 2 substituents substituted from alkyl and C1-C6- (halo) alkoxy; and the aryl, whenever mentioned, Independently of each other, it can be unsubstituted or carry one or more halogen atoms and / or independently of each other, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6- Can carry 1, 2 or 3 substituents selected from the group consisting of alkoxy and C1-C6-haloalkoxy;

R ⁷ is C1-C6-alkyl, C2-C6-alkenyl or C3-C8-cycloalkyl, where individual groups can be halogenated;
R ⁸ is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or phenyl, wherein the phenyl group is unsubstituted, can carry one or more halogen atoms, and / or Independently of each other, may carry 1, 2 or 3 substituents selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy. Can; and

R ⁹ is H or C1-C6-alkyl;
However, in Formula II, R ¹ is H and R ⁶ is as defined above; and in Formula I, (a) at least one of R ¹ and R ^{3 to} R ⁶ is hydrogen (B) R ³ or R ⁴ is in each case other than Cl when the remaining five groups of R ^{1 to} R ⁶ are hydrogen, and (c) (i) R ³ is methyl. (Ii) R ⁴ is other than Cl, (iii) R ⁵ is other than Cl, and (iv) when R ⁵ is methoxy, R ³ is not Cl and (i) to ( In the individual cases of iv), R ¹ is H, R ⁶ is MeC (═O), and the remaining groups of R ^{2 to} R ⁵ are hydrogen]
And / or a salt thereof.

Therefore, the present invention
(I) Formula I below:

[Wherein W is CR ³ ;
X is CR ⁴ ;
Y is CR ⁵ ;
R ¹ and R ⁶ are independently of each other H, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, R ⁷ C (═O) or R ⁸ HNC. (= O), where C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-Cδ-cycloalkyl, R ⁷ C (= O) or R ⁸ HNC (= O). The groups can be unsubstituted or carry one or more halogen atoms and / or independently of each other cyano, nitro, amino, OH, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkoxy, C1-C6-haloalkylthio, (C1- C6-alkoxy) carbonyl, (C1-C6-alkyl) amino, di- (C1-C6-alkyl) amino, C3-C8-cycloalkyl, C1-C6-alkylcarbonyloxy, arylcarbonyl 1, 2 or 3 groups, each selected from the group consisting of xyl and aryl, can be carried, wherein said aryl group is unsubstituted or can carry one or more halogen atoms. Can be and / or independently of one another, selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, cyano and nitro, 1, 2 or Can carry three substituents;

R ² is H;
R ³ , R ⁴ and R ⁵ are independently of each other H, halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, C2-C6-alkenyl, N- combined 4-7 membered N-containing heterocycle, C2-C6- ^{alkynyl, R 9 C (= O)} , it is a OD or aryl; where D is C1-C6- alkyl, C2-C6- alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, benzyl or aryl; the 4-7 membered heterocycle, in addition to the bonded N atom, is independently of each other C (= O), O 1, 2 or 3 heteroatoms and / or heteroatoms as ring members selected from S, N and can be substituted or unsubstituted or halogen, C1-C6- (halo ) May be substituted by 1 or 2 substituents substituted from alkyl and C1-C6- (halo) alkoxy; and the aryl, whenever mentioned, Independently of each other, it can be unsubstituted or carry one or more halogen atoms and / or independently of each other, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6- Can carry 1, 2 or 3 substituents selected from the group consisting of alkoxy and C1-C6-haloalkoxy;

R ⁷ is C1-C6-alkyl, C2-C6-alkenyl or C3-C8-cycloalkyl, where individual groups can be halogenated;
R ⁸ is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or phenyl, wherein the phenyl group is unsubstituted, can carry one or more halogen atoms, and / or Independently of each other, may carry 1, 2 or 3 substituents selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy. Can; and

R ⁹ is H or C1-C6-alkyl;
However, (a) at least one of R ¹ and R ^{3 to} R ⁶ is other than hydrogen, and (b) R ³ or R ⁴ is, in each case, the remaining five groups of R ^{1 to} R ⁶ are hydrogen. In some cases, it is other than Cl, and (c) (i) R ³ is other than methyl, (ii) R ⁴ is other than Cl, (iii) R ⁵ is other than Cl, and (iv) R ^{When 5} is methoxy, R ³ is not Cl, and in each case (i)-(iv), R ¹ is H, R ⁶ is MeC (═O), and R ² -R ⁵ The remaining group is hydrogen]; and / or a salt thereof; and

(II) Formula II below:

[Wherein W is CR ³ ;
X is CR ⁴ ;
Y is CR ⁵ ;

R ¹ is H and R ⁶ is H, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, R ⁷ C (═O) or R ⁸ HNC ( ═O), wherein the C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-Cδ-cycloalkyl, R ⁷ C (═O) or R ⁸ HNC (═O) group Can be unsubstituted or carry one or more halogen atoms and / or independently of each other cyano, nitro, amino, OH, C1-C6-alkyl, C1-C6-haloalkyl, C1 -C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkoxy, C1-C6-haloalkylthio, (C1-C6 -Alkoxy) carbonyl, (C1-C6-alkyl) amino, di- (C1-C6-alkyl) amino, C3-C8-cycloalkyl, C1-C6-alkylcarbonyloxy, arylcarbonyloxy Can carry 1, 2 or 3 groups, each selected from the group consisting of aryl and aryl, wherein the aryl group can be unsubstituted or carry one or more halogen atoms. And / or independently of one another, selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, cyano and nitro, 1, 2 or 3 Can carry one substituent;

R ² is H;
R ³ , R ⁴ and R ⁵ are independently of each other H, halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, C2-C6-alkenyl, N- combined 4-7 membered N-containing heterocycle, C2-C6- ^{alkynyl, R 9 C (= O)} , it is a OD or aryl; where D is C1-C6- alkyl, C2-C6- alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, benzyl or aryl; the 4-7 membered heterocycle, in addition to the bonded N atom, is independently of each other C (= O), O 1, 2 or 3 heteroatoms and / or heteroatoms as ring members selected from S, N and can be substituted or unsubstituted or halogen, C1-C6- (halo ) May be substituted by 1 or 2 substituents substituted from alkyl and C1-C6- (halo) alkoxy; and the aryl, whenever mentioned, Independently of each other, it can be unsubstituted or carry one or more halogen atoms and / or independently of each other, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6- Can carry 1, 2 or 3 substituents selected from the group consisting of alkoxy and C1-C6-haloalkoxy;

R ⁷ is C1-C6-alkyl, C2-C6-alkenyl or C3-C8-cycloalkyl, where individual groups can be halogenated;
R ⁸ is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or phenyl, wherein the phenyl group is unsubstituted, can carry one or more halogen atoms, and / or Independently of each other, may carry 1, 2 or 3 substituents selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy. Can; and

R ⁹ is H or C1-C6-alkyl ”and / or a salt thereof.
The compounds of formula (I) or (II) can exist in different geometric or optical isomers or tautomeric forms. The present invention protects all such isomers and tautomers, and mixtures thereof in all proportions. In particular, if the compounds of formula I have one or more chiral centers, they can exist as enantiomers or mixtures of diastereomers. The present invention provides pure enantiomers or diastereomers, their individual mixtures, and isotopic forms such as deuterides.

The organic component referred to in the definition of the above variable is a collective term for individual enumeration of individual group members. In each case, the prefix Cn-Cm indicates the possible number of carbon atoms in the group. Similarly, the term “xy member” refers to the possible number of atoms that form a closure in the corresponding ring.
The term halogen denotes in each case fluorine, bromine, chlorine or iodine.

  The term “C 1 -C 6 -alkyl” as used herein, is a saturated straight or branched carbon bonded through any of the carbon atoms having 1 to 6 carbon atoms. Reference is made to a hydride group, for example one of the following groups: 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, n-pentyl, 1, 1- Dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl , 2, 2-dimethylbutyl, 2, 3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2, 2-trimethylpropyl, 1- Ethyl-1-methylpropyl or 1- Chill-2-methylpropyl.

  The term “C1-C6-haloalkyl” as used herein is a straight chain attached through any of the carbon atoms, having from 1 to 6 carbon atoms (as mentioned above). Chain or branched chain saturated alkyl groups, where some or all of the hydrogen atoms in those groups may be replaced by fluorine, chlorine, bromine and / or iodine, ie any of the following groups To: chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-diph Oroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2, 3, 3, 3-pentafluoropropyl, heptafluoropropyl, 1- (fluoromethyl) -2-fluoroethyl, 1- (chloromethyl) -2-chloroethyl, 1- (bromomethyl) -2-bromoethyl, 4-fluoro Butyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl. Thus, the term “C1-C2-fluoroalkyl” means a C1-C2-alkyl group bearing 1, 2, 3, 4 or 5 fluorine atoms, such as difluoromethyl, trifluoromethyl, 1-fluoroethyl, Mention is made of any one of 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl or pentafluoroethyl. Use of the term “(halo)” preceding a group (ie, the term halo in parentheses) refers to the corresponding group optionally substituted with halogen, eg, the term “(halo) alkyl” Refers to an alkyl group optionally substituted with halogen.

  The term “C1-C6-alkoxy” as used herein is a straight or branched chain having 1 to 6 carbon atoms (as mentioned above) bonded through an oxygen atom. Reference is made to any one of the saturated alkyl groups on the chain, ie methoxy, ethoxy, n-propoxy, 1-methoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy or 1-dimethylethoxy. Similarly, the terms “alkenoxy”, “alkynoxy” and “benzyloxy” refer to their corresponding alkenyl, alkynyl and benzyl groups, respectively, attached through an oxygen atom.

  The term “C1-C6-haloalkoxy” as used herein is C1-C6 as mentioned above, partially or fully substituted by fluorine, chlorine, bromine and / or iodine. Means an alkoxy group, ie any one of the following groups:

  Chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2 2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2, 3- Dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-tri Fluoropropoxy, 3, 3, 3-trichloropropoxy, 2, 2, 3, 3, 3-pentaluropropoxy, heptafluoropropoxy, 1- (fluoromethyl) -2-fluoroethoxy, 1- (chloromethyl)- 2-chloroethoxy, 1- (bromomethyl) -2-bromoethoxy, 4-, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy.

  The term “C 1 -C 6” -alkylthio ”(or C 1 -C 6 -alkyl sulfanyl: C 1 -C 6 -alkyl-S—), as used herein, is attached through a sulfur atom (see above). A straight or branched alkyl group having 1 to 6 carbon atoms, i.e. methylthio, ethylthio, n-propylthio or 1,1-dimethylethylthio.

  The term “C1-C6-alkylsulfinyl” (or C1-C6-alkyl-S (= 0)-), as used herein, is attached through the sulfur atom of a sulfinyl group (see above). Refers to a straight or branched saturated alkyl group having 1 to 6 carbon atoms, ie any one of the following groups: CH3-SO, C2H5-SO, n-propyl Sulfinyl, 1-methylethyl-sulfinyl, n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, n-pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl 3-methyl-butylsulfinyl 1,1-dimethylpropylsulfinyl 1,2-dimethylpropylsulfinyl 2,2-dimethylpropylsulfin Cycloalkenyl or 1-ethylpropyl sulfinyl.

The term “C1-C6-alkylsulfonyl” (or C1-C6-alkyl-S (═O) ₂ —), as used herein, is attached through the sulfur atom of a sulfonyl group (see above). Means a straight-chain or branched saturated alkyl group having 1 to 6 carbon atoms, as defined above, ie any one of the following groups: CH3-S02, C2H5-S02, n- Propylsulfonyl, (CH3) 2CH-S02, n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl or (CH3) 3C-S02.

  The term “C1-C6-haloalkylthio” as used herein is C1-C6 as mentioned above, partially or fully substituted by fluorine, chlorine, bromine and / or iodine. -Refers to an alkylthio group, ie one of the following differences: fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromo Ethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio, 2- Chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, pentafluoroethylthio, 2-fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2,3-dichloropropylthio, 3, 3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio, heptafluoropropylthio, 1- (fluoromethyl) -2-fluoroethyl Thio, 1- (chloromethyl) -2-chloroethylthio, 1- (bromomethyl) -2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio.

  The term “C1-C6-alkoxycarbonyl” as used herein is a straight chain having 1 to 6 carbon atoms (as mentioned above) bonded through the carbon atoms of the carbonyl group. A chain or branched chain alkoxy group, ie any one of the following groups: methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, 1-methylethoxycarbonyl, n-butoxycarbonyl, 1-methylpropoxycarbonyl , 2-methylpropoxycarbonyl or 1,1-dimethylethoxycarbonyl.

  The term “C2-C6-alkenyl” as used herein is a straight chain attached through any of 2-6 carbon atoms and carbon atoms having a double bond at any position. Or a branched monounsaturated hydrocarbon group, ie any one of the following groups:

  Ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2- Propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl 2-propenyl, 1, 2-dimethyl 1-propenyl, 1, 2-dimethyl 2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3 -Hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1- Pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, 1-dimethyl 2-butenyl, 1, 1-dimethyl 3-butenyl, 1, 2-dimethyl l-butenyl, 1, 2-dimethyl 2-butenyl, 1, 2-dimethyl 3-butenyl, 1, 3-dimethyl 1- Butenyl, 1,3-dimethyl 2-butenyl, 1,3-dimethyl 3-butenyl, 2,2-dimethyl 3-butenyl, 2,3-dimethyl 1-butenyl, 2,3-dimethyl 2-butenyl, 2,3 -Dimethyl 3-butenyl, 3,3-dimethyl 1-butenyl, 3,3-dimethyl 2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2- ethyl 1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1, 1, 2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2 -Methyl-1-propenyl or 1-ethyl-2-methyl-2-propenyl.

  The term “C2-C6-alkynyl”, as used herein, includes a CC triple bond and has 2 to 6 carbon atoms, bonded through any of the carbon atoms, linear or Mention may be made of branched-chain hydrocarbon radicals, for example one of the following groups: ethynyl, prop-1-in-1-yl, prop-2-in-1-yl, n-but-1- In-1-yl, n-but-1-in-3-yl, n-but-1-in-4-yl, n-but-2-in-1-yl, n-pent-1-in- 1-yl, n-pent-1-in-3-yl, n-pent-1-in-4-yl, n-pent-1-in-5-yl, n-pent-2-in-1- Yl, n-pent-2-yn-4-yl, n-pent-2-yn-5-yl, 3-methylbut-1-in-3-yl, 3-methylbut-1-in-4-yl, n-hex-1-in-1-yl, n-hex-1-in-3-yl, n-hex-1-in-4-yl, n-hex-1-yn-5-yl, n- Hexe-1-in-6-yl N-hex-2-yn-1-yl, n-hex-2-yn-4-yl, n-hex-2-yn-5-yl, n-hex-2-yn-6-yl, n -Hexe-3-in-1-yl, n-hex-3-in-2-yl, 3-methylpent-1-in-1-yl, 3-methylpent-1-in-3-yl, 3-methylpent -1-In-4-yl, 3-methylpent-1-in-5-yl, 4-methylpent-1-in-1-yl, 4-methylpent-2-in-4-yl or 4-methylpent-2 -In-5-yl and the like.

  The term “C3-C8-cycloalkyl” as used herein is a monocyclic hydrocarbon group having 3 to 8 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclo-hexyl, Reference is made to either one of cycloheptyl or cyclooctyl.

  The term “(C1-C6-alkyl) amino” as used herein has 1 to 6 carbon atoms (as mentioned above) bonded through the nitrogen atom of the amino group. Straight or branched saturated alkyl groups, i.e. methylamino, ethylamino, n-propylamino, 1-methylethylamino, n-butylamino, 1-methylpropylamino, 2-methylpropylamino or 1, Mention is made of any one of 2-dimethylethylamino.

  The term “di (C1-C6-alkyl) amino” as used herein, is from 1 to 6 carbon atoms (as mentioned above) each bonded through the nitrogen atom of the amino group. Refers to two straight-chain or branched saturated alkyl groups having, for example, any one of the following groups:

N _, N-dimethylamino, N, N-diethylamino, N, N-di (1-methylethyl) amino, NN-dipropylamino, N _, N-dibutylamino, N, N-di- (1-methylpropyl) ) Amino, N, N-di- (2-methylpropyl) amino, N _, N-di- (1,1-dimethylethyl) amino, N-ethyl-N-methylamino, N-methylN-propylamino, N-methyl N- (1-methylethyl) amino, N-butyl-N-methylamino, N-methyl N- (1-methylpropyl) -amino, N-methyl N- (2-methylpropyl) amino, N -(1,1-dimethylethyl) -N-methylamino, N-ethyl-N-propylamino, N-ethyl-N- (1-methylethyl) amino, N-butyl-N-ethylamino, N-ethyl -N- (1-methylpropyl) amino, N-ethyl-N- (2-methylpropyl) amino, N-ethyl-N- (1,1-dimethylethyl) amino, N- (l-methylethyl)- N-propylamino, N-butyl- N-propylamino, N- (1-methylpropyl) -N-propylamino, N- (2-methylpropyl) -N-propylamino, N- (1,1-dimethylethyl) -N-propylamino, N -Butyl-N- (1-methylethyl) amino, N- (1-methylethyl) -N- (1-methylpropyl) -amino, N- (1-methylethyl) -N- (2-methylpropyl) Amino, N- (1,1-dimethylethyl) -N- (1-methylethyl) amino, N-butyl-N- (1-methylpropyl) amino, N-butyl-N- (2-methylpropyl) amino , N-butyl-N- (1,1-dimethylethyl) amino, N- (1-methylpropyl) -N- (2-methylpropyl) amino, N- (1,1-dimethylethyl) -N- ( 1-methylpropyl) amino or N- (1,1-dimethylethyl) -N- (2-methylpropyl) -amino.

  The term “C1-C6-alkylcarbonyloxy” as used herein, is a straight or branched chain saturated chain having 1 to 6 carbon atoms attached through the oxygen atom of the carbonyl group. Alkyl groups (as mentioned above), i.e. methyl C (= O) O, ethyl C (= O) O, n-propyl C (= O) O, 1-methylethyl C (= O) O, n-butyl C (= O) O, 1-methylpropyl C (= O) O, 2-methylpropyl C (= O) O or 1,2-dimethylethyl C (= O) O means.

  The term “aryl” (and also in arylcarbonyloxy) as used herein refers to an aromatic hydrocarbon ring that may be mono-, bi- or tricyclic. Examples of such rings include phenyl, naphthalenyl, anthracenyl, indenyl or phenanthrenyl. A preferred aryl group is phenyl (Ph).

  The term “aryl-C1-C6-alkyl” as used herein (and also C3-C8-cycloalkyl-C1-C6-alkyl, heteroaryl-C1-C6-alkyl, heterocyclic, -C1-C6-alkyl), each group attached to the rest of the molecule through any carbon atom of a C1-C6-alkylene group. Examples of preferred “aryl-C1-C6-alkyl” are benzyl, 1-phenylethyl and 2-phenylethyl. Similarly, aryl-C2-C6-alkenyl and aryl-C2-C6-alkynyl are aryl bonded to the rest of the molecule through any carbon atom of the C2-C6-alkenylene and C2-C6-alkynylene groups, respectively. Means group.

  The term “N-attached 4-7 membered heterocycle containing N atoms” means each group attached to the rest of the molecule through a ring nitrogen atom. Heterocyclic compounds can be saturated, partially unsaturated or aromatic cyclic groups having one or more rings, preferably one ring. The 4- to 7-membered heterocyclic group is independently selected from C (= 0), O, S and N, in addition to the N atom to which it is attached, 1, 2 or 3 as ring members. Individual heteroatoms and / or heteroatoms. Heterocycles can be substituted or unsubstituted and examples of substituents include halogen, C1-C6- (halo) alkyl, C1-C6- (halo) alkoxy. In a preferred embodiment, the 4-7 membered heterocycle is an unsubstituted 5- or 6-membered ring having one other heteroatom or heteroatom group.

  Examples include 4-6 membered lactams linked by an N atom, examples of which are β-lactams, γ-lactams and δ-lactams such as 2-oxo-pyrrolidin-1-yl or 2- Oxo-piperidin-1-yl; unsaturated heterocycles such as pyrrol-1-yl, pyrazol-1-yl, 1,2,4-triazolyl-1-yl, 1,2,3-triazolyl-1-yl, And tetrazol-1-yl, tetrazol-2-yl; and saturated heterocycles such as piperidin-1-yl, morpholin-4-yl or thiomorpholin-4-yl.

  In preferred embodiments, the C1-C6 moiety is a C1-C6-alkyl substituent or group such as C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-alkylsulfonyl, When indicated as C1-C6-alkylsulfinyl, C1-C6-haloalkylthio, C1-C6-haloalkyl, (C1-C6-alkyl) amino, di (C1-C6-alkyl) amino, etc. Regardless, it is a C1-C4-component, preferably a C1-C3-component, such as any one of C1-component, C2-component or C3-component. If more than one alkyl component is present, the chain length can be different.

  In preferred embodiments, the C2-C6-components are those, for example, C2-C6-alkenyl substituents or groups, C2-C6-alkynyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C2-C6-alkynyl. Whenever indicated as oxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, etc., regardless of the type of component, C2-C5-component, preferably C2-C4-component, such as C2-component, C3 -One of the component or the C4 component.

In preferred embodiments, the C3-C8 component is related to the type of component whenever it represents, for example, a C3-C8-cycloalkyl substituent or group, C3-C8-cyclohaloalkyl, C3-C8-cycloalkoxy, etc. Rather, it is a C3-C5-component, such as either a C3-component or a C5-component.
In one embodiment, with respect to compounds of formula I, R ¹ -R ⁶ are as defined in the first aspect, provided that (i) R ³ is not Cl or Me and (ii) R ⁴ is Cl But (iii) R ⁵ is not Cl 2 and (iv) R ³ is not Cl when R ⁵ is methoxy, and R ^{2 to} R ⁵ in each case (i) to (iv) The remaining group is hydrogen.

In one embodiment, with respect to compounds of formula I, when R ¹ is H and any one of R ^{3 to} R ⁵ is Cl 2 or methyl, R ⁶ is other than H or CH ₃ C (═O) It is.
In one embodiment, with respect to compounds of formula I, R ¹ and R ⁶ are as defined in the first aspect, and one of —R ^{3 to} R ⁵ is other than hydrogen, and the substituents is other than Cl and Me, and two of -R ³ to R ⁵ is other than hydrogen, one of the substituents is other than methoxy.
In one embodiment, for the compound of formula I, R ^{1 to} R ⁶ are as defined in the first aspect, provided that R ^{3 to} R ⁵ are other than Cl and Me, preferably halogen and C ^1- Other than C3- (halo) alkyl.

In one embodiment, with respect to compounds of formula I, when any one of R ³ -R ⁵ is halogen or C1-C3- (halo) alkyl, one of R ¹ and R ⁶ is H and C1-C3 Other than-(halo) alkyl-C (= O).
In one embodiment, for the compounds of formula I, H and CH ₃ C (═O) are not substituents on either R ¹ or R ⁶ .
Regardless of the other embodiment, in one embodiment, any two of R ^{3 to} R ⁵ are H. Preferably R ³ and R ⁴ are H and R ⁵ is as defined in the first aspect.

Independent of other embodiments, in one embodiment, with respect to Formula I or II, R ³ is C1-C4-alkyl.
Regardless of the other embodiment, in one embodiment, with respect to Formula I or II, any two of R ³ , R ^4, and R ⁵ are H.
Independent of other embodiments, in one embodiment, with respect to Formula I or II, R ³ and R ⁴ are H.

Independent of other embodiments, in one embodiment, with respect to Formula I or II, R ¹ is H.
Independent of other embodiments, in one embodiment, with respect to compounds of formula I, R1 is H or C1-C6-alkyl.
Independent of other embodiments, in one embodiment, with respect to Formula I or II, R ¹ is C1-C6-alkyl.

Independent of other embodiments, in one embodiment, with respect to Formula I or II, R ⁶ is H, C 2 -C ⁶ -alkynyl, R ⁷ C (═O), R ⁸ HNC (═O) and C 1 -C 6. Selected from -alkyl, wherein the C1-C6-alkyl group may be substituted by cyano, C1-C6-alkoxy, C3-C8-cycloalkyl or aryl, and the C2-C6-alkynyl, R ⁷ C ( = O), R ⁸ HNC (= O), and C1-C6-alkyl groups can carry one or more halogen atoms. Preferably R ⁶ is H, C1-C3- (halo) alkyl and C1-C3- (halo) alkylC (═O).

Regardless of the other embodiment, in one embodiment, R ⁵ is halogen, C1-C6-alkyl or C1-C6-haloalkyl.
Regardless of the other embodiment, in one embodiment, R ¹ , R ⁶ , R ² , R ³ and R ⁴ in Formula I are each H and R ⁵ is halogen, CN or aryl, said aryl Can be unsubstituted or carry one or more halogen atoms and / or independently of each other, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1 -C6- haloalkoxy, can carry one, two or three substituents selected from the group consisting of R ⁹ C (= O). In a preferred embodiment, R ⁵ is halogen.

Regardless of the other embodiment, in one embodiment, R ¹ , R ² , R ³ and R ⁴ in Formula II are each H, R ⁶ is C1-C6-alkyl, and R ⁵ is halogen. is there.
Specific examples of Formula I are disclosed in the table below.

Specific examples of Formula I are disclosed in the table below.
Table 1.1 : Compounds of formula (I) wherein R1, R2 and R6 are H and the values for W, X and Y are as given in Tables 1 to 4;
Table 1.2: R1 is CH ₃ - and is, R2 and R6 are H, and W, the values for X and Y are as given in Table 1 to Table 4, compounds of formula (I);
Table 1.3: R1 is CH ₃ CH ₂ - and is, R2 and R6 are H, and W, the values for X and Y are as given in Table 1 to Table 4, compounds of formula (I);
Table 1.4 : R1 is CH ₃ CH ₂ CH ₂ —, R 2 and R 6 are H, and the values for W, X and Y are as given in Tables 1 to 4, in formula (I) Compound;
Table 1.5 : R1 is (CH ₃ ) ₂ CH—, R2 and R6 are H, and the values for W, X and Y are as given in Tables 1 to 4, in formula (I) Compound;

Table 1.6: R1 is _{CH 3 CH 2 CH 2 CH 2} - is, R2 and R6 are H, and W, the values for X and Y are as given in Table 1 to Table 4, the formula (I ) Compounds;
Table 1.7 : R1 is (CH ₃ ) ₂ CH ₂ CH _2- , R2 and R6 are H, and the values for W, X and Y are as given in Tables 1 to 4, formula ( Compounds of I);
Table 1.8: R1 is NCCH ₂ - a, R2 and R6 are H, and W, the values for X and Y are as given in Table 1 to Table 4, compounds of formula (I);
Table 1.9: R1 is cyclopropyl -CH ₂ - and is, R2 and R6 are H, and W, the values for X and Y are as given in Table 1 to Table 4, the compound of formula (I) ;
Table 1.10 : R1 is CH ₃ OCH ₂ CH ₂ —, R2 and R6 are H, and the values for W, X and Y are as given in Tables 1 to 4, in formula (I) Compound;

Table 1.11 : R1 is H ₂ C═CHCH ₂ —, R2 and R6 are H, and the values for W, X and Y are as given in Tables 1 to 4, in formula (I) Compound;
Table 1.12 : R1 is H ₂ C≡CCH ₂ —, R2 and R6 are H, and the values for W, X and Y are as given in Tables 1 to 4, in formula (I) Compound;
Table 1.13: R1 is phenyl -CH ₂ - is, R2 and R6 are H, and W, the values for X and Y are as given in Table 1 to Table 4, compounds of formula (I);
Table 1.14: R2 is H, R1 and R6 is CH _3, and W, the values for X and Y are as given in Table 1 to Table 4, compounds of formula (I);
Table 1.15 : R1 is H ₂ C≡CCH ₂ —, R2 is H, R6 is CH ₃ and the values for W, X and Y are as given in Tables 1 to 4. A compound of formula (I);

Table 1.16: R1 is CH ₃ CH ₂ - and is, R2 is H, R6 is CH _3, and W, the values for X and Y are as given in Tables 1 to 4, wherein ( Compounds of I);
Table 1.17: R1 is CH ₃ CH ₂ CH ₂ - and is, R2 is H, R6 is CH _3, and W, the values for X and Y are as given in Tables 1 to 4, A compound of formula (I);
Table 1.18: R1 is (CH _{3) 2} CH- and is, R2 is H, R6 is CH _3, and W, the values for X and Y are as given in Tables 1 to 4, A compound of formula (I);
Table 1.19: R1 is _{CH 3 CH 2 CH 2 CH 2} - is, R2 is H, R6 is CH _3, and W, the values for X and Y are as given in Table 1 to Table 4 A compound of formula (I);
Table 1.20 : R1 is (CH ₃ ) ₂ CH ₂ CH ₂ —, R2 is H, R6 is CH ₃ and the values for W, X and Y are as given in Tables 1 to 4 A compound of formula (I);

Table 1.21 : R1 is NCCH ₂ —, R2 is H, R6 is CH ₃ and the values for W, X and Y are as given in Tables 1 to 4, Formula (I) A compound of
Table 1.22: R1 is cyclopropyl -CH ₂ - and is, R2 is H, R6 is CH _3, and W, the values for X and Y are as given in Tables 1 to 4, wherein A compound of (I);
Table 1.23: R1 is phenyl -CH ₂ - is, R2 is H, R6 is CH _3, and W, the values for X and Y are as given in Tables 1 to 4, wherein ( Compounds of I);
Table 1.24: R2 is H, R1 and R6 CH ₃ CH ₂ - is, and W, the values for X and Y are as given in Table 1 to Table 4, compounds of formula (I);
Table 1.25: R2 is H, R1 is CH ₃ OCH ₂ CH ₂ - is, R6 is CH ₃ CH ₂ - as a and, and W, the value of X and Y given in Tables 1 to 4 A compound of formula (I);

Table 1.26 : R2 is H, R1 is HC≡CCH ₂ —, R6 is CH ₃ CH ₂ —, and the values for W, X and Y are as given in Tables 1-4. A compound of formula (I);
Table 1.27: R2 is H, R1 is CH ₃ CH ₂ CH ₂ - is, R6 is CH ₃ CH ₂ - as a and, and W, the value of X and Y given in Tables 1 to 4 A compound of formula (I);
Table 1.28: R2 is H, R1 is (CH _{3) 2} CH- and is, R6 is CH ₃ CH ₂ - as a and, and W, the value of X and Y given in Tables 1 to 4 A compound of formula (I);
Table 1.29: R2 is H, R1 is _{CH 3 CH 2 CH 2 CH 2} - is, R6 is CH ₃ CH ₂ - and is, and W, the values for X and Y are given in Table 1 to Table 4 A compound of formula (I) as is;
Table 1.30 : R2 is H, R1 is (CH ₃ ) ₂ CH ₂ CH _2- , R6 is CH ₃ CH _2- , and values for W, X and Y are given in Tables 1 to 4 A compound of formula (I), as given;

Table 1.31 : R2 is H, R1 is NCCH ₂ —, R6 is CH ₃ CH ₂ —, and the values for W, X and Y are as given in Tables 1 to 4, A compound of (I);
Table 1.32: R2 is H, R1 is cyclopropyl -CH ₂ - is, R6 is CH ₃ CH ₂ - and is, and W, the values for X and Y are as given in Table 1 to Table 4 A compound of formula (I);
Table 1.33: R2 is H, R1 is phenyl -CH ₂ - is, R6 is CH ₃ CH ₂ - and is, and W, the values for X and Y are as given in Table 1 to Table 4 A compound of formula (I);
Table 1.34 : R1 is CH ₃ (C═O) —, R2 and R6 are H, and the values for W, X and Y are as given in Tables 1 to 4, Formula (I) A compound of
Table 1.35 : R1 is CH ₃ CH ₂ (C═O) —, R2 and R6 are H, and the values for W, X and Y are as given in Tables 1 to 4, formula ( Compounds of I);

Table 1.36: R1 is _{CH 3 CH 2 CH 2 (C} = O) - and is, R2 and R6 are H, and W, the values for X and Y are as given in Tables 1 to 4, A compound of formula (I);
Table 1.37: R1 is _{(CH 3) 2 CH (C} = O) - and is, R2 and R6 are H, and W, the values for X and Y are as given in Tables 1 to 4, A compound of formula (I);
Table 1.38: R1 is _{CH 3 CH 2 CH 2 CH 2} (C = O) - and is, R2 and R6 are H, and W, the values for X and Y are as given in Table 1 to Table 4 A compound of formula (I);
Table 1.39: R1 is _{(CH 3) 2 CH 2 CH} 2 (C = O) - and is, as R2 and R6 is H, and W, the value of X and Y given in Tables 1 to 4 A compound of formula (I);
Table 1.40 : R1 is CH ₃ NH (C═O) —, R2 and R6 are H, and the values for W, X and Y are as given in Tables 1 to 4, formula (I ) Compounds;

Table 1.41: R1 is _{CH 3 CH 2 NH (C =} O) - and is, R2 and R6 are H, and W, the values for X and Y are as given in Tables 1 to 4, wherein A compound of (I);
Table 1.42: R1 is _{CH 3 CH 2 CH 2 NH (} C = O) - and is, R2 and R6 are H, and W, the values for X and Y are as given in Table 1 to Table 4 A compound of formula (I);
Table 1.43: R1 is _{(CH 3) 2 CHNH (C} = O) - and is, R2 and R6 are H, and W, the values for X and Y are as given in Tables 1 to 4, A compound of formula (I);
As a and, R2 and R6 are H, and W, the value of X and Y given in Tables 1 to 4 - R1 is _{CH 3 CH 2 CH 2 CH 2} NH (C = O): Table 1.44 A compound of formula (I);
Table 1.45: R1 is _{(CH 3) 2 CH 2 CH} 2 NH (C = O) - and is, R2 and R6 are H, and W, the values for X and Y are given in Tables 1 to 4 A compound of formula (I):

Table 1.46 : R1 is phenyl NH (C═O) —, R2 and R6 are H, and the values for W, X and Y are as given in Tables 1 to 4, Formula (I) A compound of
Table 1.47: R1 is CH ₃ OC ₂ H ₅ - a and, R2 is H, R6 is CH _3, and W, the values for X and Y are as given in Tables 1 to 4, A compound of formula (I);
Table 1.48: R1 is CH ₂ = CHCH ₂ - and is, R2 is H, R6 is CH _3, and W, the values for X and Y are as given in Tables 1 to 4, wherein Compound of (I);
Table 1.49 : R1 is CH ₂ = CHCH _2- , R2 is H, R6 is CH ₃ CH _2- , and the values for W, X and Y are as given in Tables 1 to 4 A compound of formula (I);

Table 2.1 : Compounds of formula (II), wherein R 1 and R 2 are H, R 6 is CH ₃ OCH ₂ — and the values for W, X and Y are as given in Tables 1 to 4;
Table 2.2: R6 is CH ₃ - and is, R1 and R2 are H, and W, the values for X and Y are as given in Table 1 to Table 4, the compound of formula (II);
Table 2.3: R6 is CH ₃ CH ₂ - and is, R1 and R2 are H, and W, the values for X and Y are as given in Table 1 to Table 4, the compound of formula (II);
Table 2.4 : R6 is CH ₃ CH ₂ CH ₂ —, R 1 and R 2 are H, and the values for W, X and Y are as given in Tables 1 to 4, in formula (II) Compound;
Table 2.5 : R6 is (CH ₃ ) ₂ CH—, R1 and R2 are H, and the values for W, X and Y are as given in Tables 1 to 4, in formula (II) Compound;

Table 2.6: R6 is _{CH 3 CH 2 CH 2 CH 2} - is, R1 and R2 are H, and W, the values for X and Y are as given in Table 1 to Table 4, the formula (II ) Compounds;
Table 2.7 : R6 is (CH ₃ ) ₂ CH ₂ CH ₂ —, R 1 and R 2 are H, and the values for W, X and Y are as given in Table 1 to Table 4, Compounds of II);
Table 2.8: R6 is NCCH ₂ - a, R1 and R2 are H, and W, the values for X and Y are as given in Table 1 to Table 4, the compound of formula (II);
Table 2.9 : Compounds of formula (II), wherein R6 is HC≡CCH ₂ —, R1 and R2 are H, and the values for W, X and Y are as given in Tables 1 to 4;
Table 2.10 : R6 is H ₂ C═CHCH ₂ —, R1 and R2 are H, and the values for W, X and Y are as given in Tables 1 to 4, in formula (II) Compound;

Table 2.11: R6 is cyclopropyl -CH ₂ - is, R1 and R2 are H, and W, the values for X and Y are as given in Table 1 to Table 4, the compound of formula (II) ;
Table 2.12: R6 is phenyl -CH ₂ - is, R1 and R2 are H, and W, the values for X and Y are as given in Table 1 to Table 4, the compound of formula (II);
Table 2.13 : R1 and R2 are H, R6 is CH ₃ OCH ₃ CH ₂ — and the values for W, X and Y are as given in Tables 1 to 4, in formula (II) Compound.

The following components, compounds of formula I, preferably compounds of formulas I and II, are excluded from the scope of the present invention:
Each of R ^{1 to} R ⁶ is H;
When R ¹ , R ² , R ³ , R ⁵ and R ⁶ are each H, then R ⁴ is other than Cl;
When R ¹ , R ² , R ⁴ , R ⁵ and R ⁶ are each H, then R ³ is other than Cl;
When R ¹ , R ² , R ⁴ and R ⁵ are each H and R ⁶ is acyl, then R ³ is other than methyl;
When R ¹ , R ² , R ³ and R ⁵ are each H and R ⁶ is acyl, then R ⁴ is other than Cl;
When R ¹ , R ² , R ³ and R ⁴ are each H and R ⁶ is acyl, then R ⁵ is other than Cl; and
When R ¹ , R ² and R ⁴ are each H, R ⁵ is methoxy and R ⁶ is acyl, R ³ is other than Cl.

The compound of formula I, wherein W, X, Y, R ² , R ¹ and R ⁶ are as defined in the first aspect, is 3-chloro-benzo [d] -isothiazole 1,1-dioxide It can be prepared by reacting A with a primary or secondary amine B. Hal is halogen, preferably chlorine or bromine, most preferably chlorine.

  These reactions are for example published by Duphar (EP33984) or BASF (WO07113119), or CWWhitehead, Journal of Organic Chemistry, 25, 413-16; 1960 or HB Rode, Pharmazie, 60 (10), 723- 731; 2005, and can be performed analogously to standard methods described in the past.

3-Chloro-benzo [d] -isothiazole 1,1-dioxide A can be used as described by HB Rode, Pharmazie, 60 (10), 723-731; It can be prepared by reacting SOCl ₂ , PCl ₅ / POCl ₃ .

Hal is chlorine, W is CH, X is CH, and Y is C—CH ₃ or CF, compound A is novel and an intermediate for the preparation of its corresponding active ingredient Can be used as
Substituted saccharin C is as described by Desai, Ranjit C, Journal of Organic Chemistry (1994), 59 (23), 7161-3 or Naoyuki Masuda, Bioorgaic & Medicinal Chemistry 13 (2005) 949-961. , 2-chlorosulfonyl-benzoate D can be prepared by reacting with ammonia.

  The latter document also describes the synthesis of 2-chlorosulfonyl-benzoate D from its corresponding methyl anthranilate E through diazotization and subsequent chlorosulfonylation. A similar method is described by M. L. Trudell et al. In Journal of Heterocyclic Chemistry, 2004, 41, 435-438.

If methyl anthranilate E is not commercially available, they can be obtained by catalytic hydrogenation as described by JFW Keana et al. In Bioorganic & Medicinal Chemistry 1 1 (2003) 1769-1780 or by FH Jung, J. Med. Chem. 2006, 49, 955-970 or MH Rabinowitz et al., J. Med. Chem. 2006, 49, 6371-6390, as described by SnCl ₂ or Na ₂ (S ₂ O ₄ ). Such a reducing agent can be prepared from its corresponding 2-nitrobenzoic acid methyl ester.

  On the other hand, saccharin (C) can be obtained from its corresponding Nt-butyl saccharin by heating with a strong acid similar to that described by KF Burri, Helvetica Chimia acta, 1990, 73, 69-80, such as trifluoroacetic acid. Can be prepared by cleavage of G.

  Nt-Butylsaccharin G can be obtained from the formula J (R6 is t-butyl) by directed ortho metallization with a base such as butyl lithium or lithium diisopropylamino and subsequent trapping of the metallized species with carbon dioxide under ring closure. Of the compound). Said method is described by D. Becker et al., Tetrahedron, 1992, 2515-2522. Metallization can be performed as described by N. Murugesan et al., Journal of Medicinal Chemisry, 1998, 41, 5198-5212.

  On the other hand, compounds of formula I (wherein W, X, Y, R2, R1 and R6 are as defined in the first aspect) can be prepared using standard methods such as acylation, reaction with isocyanates or reduction. It can be prepared from a compound of formula (Ia) using sex amination. Similar transformations have already been described in publications by EP33984 (Duphar).

  Compounds of formula (Ia) or (IIa) can be prepared from sulfonyl chlorides through sulfonamides H or K by cyclization under basic conditions.

  On the other hand, the compound of formula (I), wherein W, X, Y, R2 and R1 are as defined in the first aspect and R6 is hydrogen, is a primary amine at high temperature. Can be prepared from compounds of formula M through reaction with The reaction can be carried out purely or in a suitable solvent, preferably a polar high-boiling solvent such as THF or dioxane. Preferably the reaction is carried out purely. When the reaction is carried out purely, the preferred temperature is from room temperature to the boiling point of the amine. When the reaction is carried out in a solvent, the preferred temperature is from room temperature to the boiling point of the solvent. The substituent R99 in this process is preferably an alkyl substituent such as methyl or ethyl.

  Similar to the method described by R.F. Meyer, Journal of Organic Chemistry, 1963, 28, 2902-2903, an imidate compound of formula M is obtained by reaction of a sulfonamide of formula H with a carbonic acid orthoester.

The novel 2-cyano-sulfonyl halide L can be prepared by the methods described below.
Similar to the standard method described in publication WO07 / 014913 (according to BASF), compounds L, N, O and P are defined as compounds Q (W, X, Y and R2 are defined in the first aspect. Can be prepared starting from

  On the other hand, sulfonyl halides of formula L can be prepared from amino compounds of formula R.

The amino group in compound R is converted to its corresponding diazonium salt, followed by reaction of the diazonium salt with dioxide in the presence of cupric chloride to give sulfonyl chloride L.
Suitable nitrosating agents are nitrosium tetrafluoroborate, nitrosyl chloride, nitrosylsulfuric acid, alkyl nitrites such as tert-butylnitrite, or salts of nitrite such as sodium nitrite. Preferably sodium nitrite is used.

Generally, sulfur dioxide is dissolved in glacial acetic acid.
The diazonium salt also reacts with a mixture of cuprous cyanide and sodium cyanide to give the cyanate compound, which is treated with sodium sulfide to give the disulfide compound. The disulfide compound is converted to sulfonyl chloride L by nitrous acid in the presence of chlorine.

A compound of formula L (where Hal is chlorine, W is CH, X is CH and Y is CF) or formula L (where Hal is chlorine and W is C- is CH _3, X is CH, Y is a compound of a C-CH ₃₎ are novel and can be used as intermediates for the preparation of the corresponding active ingredient.
If amino compounds of formula R are not commercially available, they can be prepared from its corresponding 2-nitro compound by analogous methods as described for the preparation of amino compound E.

  On the other hand, an amino compound of formula R is obtained from a compound of formula T through an oxime of formula U as described by James B. Campbell, Synthetic Communications (1989), 19 (13-14), 2255-63. Can be prepared.

Compounds of formula (I) or (II) can be prepared by a metal catalyzed cross-coupling reaction such as cyanation, Sonogashira, Stille, Heck or Suzuki cross-coupling reactions, for example by formula (I) or (II) (formula In which any one of W, X and Y is C-halogen, and halogen is chlorine, bromine or iodine). These reactions can be performed analogously to standard methods described in the literature. Many examples can be found in the reference book “Metal Catalyzed Cross Coupling Reactions” 2nd ed .; Diederich, F., de Meijere, A., Eds .; Wiley-VCH: Weinheim, Germany, 2004.
As an example, the introduction of the group R5 is shown in the following scheme:

One skilled in the art will appreciate that appropriate changes to the above reaction conditions may be required for a particular cyano-substituted phenyl compound and its corresponding nitrogen derivative compound of Formula I or II.
Compounds of formula I or II are each replaced by another compound of formula I or II by substituting one or more substituents of the starting compound of formula I or II, respectively, with other substituents according to the invention. It can be converted in a manner known per se.

  Depending on the reaction conditions and the choice of starting materials that are appropriate in each case, it is possible in one reaction step, or many, to simply substitute one substituent with another substituent of the invention. Can be substituted with other substituents of the present invention in the same reaction step.

  Salts of compounds of formula I or II can be prepared in a manner known per se. Thus, for example, acid addition salts of compounds of Formula I or II are obtained by treatment with a suitable acid or suitable ion exchange reagent, and base addition salts are obtained by treatment with a suitable base or suitable ion exchange reagent. .

  A salt of a compound of formula I or II can be converted to a free compound of formula I or II, ie an acid addition salt, respectively, by treatment with a suitable base compound or a suitable ion exchange reagent, and a suitable acid or suitable ion. It can be converted to a base addition salt by treatment with an exchange reagent.

  The salts of the compounds of the formula I or II are in a manner known per se, the inorganic salts formed by silver chloride are insoluble and thus suitable metal salts, such as, for example, in a suitable solvent that precipitates from the reaction mixture. Can be converted to other salts, acid addition salts, eg other acid addition salts of the compounds of formula I or II, respectively, by sodium, barium or silver salts of the acid, eg by silver acetate, by salts of inorganic acids, eg hydrochloride .

Depending on the procedure or reaction conditions, the compounds of formula I or II having salt-form properties are obtained in free or salt form.
Suitable salts of the compounds of formula I or II for use according to the invention are in particular agriculturally acceptable salts. They can be formed in the usual way, for example by reacting the compound with the acid of the anion in question.

  Suitable agriculturally useful salts are in particular salts of their cations or acid addition salts of their acids, whose cations and anions are those of harmful insects, arachnids and / or nematodes. It does not have any adverse effect on the action of the compounds of the invention that are useful for attack. Thus, suitable cations are in particular alkali metals, preferably lithium, sodium and potassium, alkaline earth metals, preferably calcium, magnesium and barium, and transition metals, preferably manganese, copper, zinc and iron ions, and also If desired, ammonium ions carrying 1 to 4 C1-C4-alkyl substituents and / or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, Furthermore, phosphonium ions, sulfonium ions, preferably tri (C1-C4-alkyl) sulfonium, and sulfoxonium ions, preferably tri (C1-C4-alkyl) sulfoxonium.

  Useful acid addition salt anions are mainly chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrate, hydroxide, hydrogen phosphate, phosphate, nitrate, carbonate Hydrogen salts, carbonates, hexafluorosilicates, hexafluorophosphates, benzoates, and C1-C4-alkali acid anions, preferably formate, acetate, propionate and butyrate. They can be formed by reacting a compound of formula I with its corresponding anionic acid, preferably hydrochloric acid, odoric acid, sulfuric acid, phosphoric acid or nitric acid. Suitable salts also include the adducts of formula I, such as maleic acid, dimaleic acid, fumaric acid, difumaric acid and methanesulfonic acid.

  Compounds of formula I or II and, where appropriate, their tautomers (in each case in free or salt form) are in the form of one of the possible isomers or as a mixture thereof, for example Asymmetry present in the molecule in the form of pure isomers, e.g. enantiomers and / or diastereomers, or as isomer mixtures, e.g. enantiomer mixtures, e.g. racemates, diastereomeric mixtures or racemic mixtures. Depending on the number, absolute and relative shape of the carbon atoms and / or depending on the shape of the non-aromatic double bond present in the molecule, the present invention may be a pure isomer. And also for all possible isomeric mixtures, and the details of the stereochemistry should be understood in the meaning described above and below, even in the individual case, even if not specifically mentioned.

  Diastereomeric or racemic mixtures of the compounds of the formula I or II in free or salt form, which are obtained depending on the starting materials and methods selected, can be obtained, for example, by fractional conjugation, distillation and / or chromatography. Based on the physiochemical differences of the components, the pure diastereomers or racemates can be separated in known manner.

  Enantiomeric mixtures obtained in a similar manner, for example racemates, are chromatographed on chiral adsorbents by known methods, for example by recrystallization from optically active solvents, for example with the aid of suitable microorganisms. When only one enantiomer is complexed by high performance liquid chromatography (HPLC) on acetylcellulose, a specific immobilized enzyme is used through the formation of an inclusion compound using a chiral crown ether. In order to obtain diastereomers which can be liberated by decomposition by the action of or by the action of a suitable agent, for example the action of a basic agent, the racemate of the basic end product and the optically active acid, carboxylic acid Reacting, for example, camphoric acid, tartaric acid, malic acid or sulfonic acid, and the diastereomeric mixture obtained in this way is By separation by fractional crystallization based on the solubility, it can be decomposed into an optical enantiomer.

  Pure diastereomers or enantiomers are obtained not only by separation of appropriate isomer mixtures, but also by generally known methods of diastereoselective or enantioselective synthesis, e.g. of appropriate stereochemistry. It is obtained according to the invention by carrying out the process of the invention with starting materials.

  Where individual components have different biological activities, in each case a biologically more effective isomer, such as an enantiomer or diastereomer, or an isomer mixture, such as an enantiomeric mixture or diastereomer. It is convenient to isolate or synthesize the mer mixture.

  In individual cases, compounds of formula I or II in free or salt form and where appropriate their tautomers are also obtained in hydrate form, if appropriate, and / or other solvents such as solids Includes those that have been used for the crystallization of compounds that exist in form.

New intermediate compounds to compounds of formula I or II are also available herein.
The compounds of the formula I or II according to the invention have a very favorable biocidal range and are prophylactic in the field of pest control even at low application rates, well tolerated by warm-blooded species, fish and plants. And / or a therapeutically valuable active ingredient. The active ingredients according to the invention are usually sensitive but also act against all or individual developmental stages of animal pests that are resistant, for example insect or mite representatives. The insecticidal or acaricidal activity of the active ingredients according to the invention can be directly, i.e. immediately after the passage of time, or simply thereafter, e.g. during molting, in the destruction of pests or indirectly, e.g. reduced egg production and / or Or in the good activity corresponding to the hatching rate, ie the destruction rate (death rate) of at least 50-60%.

  The compounds of formula I or II and their compositions are suitable for the effective control of insect nets, spider webs and / or roundworm net pests, especially in crop protection. In particular, they are suitable for controlling the following insect pests:

  Lepidoptera (Lepidoptera), such as Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argylesia res -Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristola fumiuma furiuma (Choristoneura occidentalis), Sirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diafania nichidari (Diaphania nitidalis), Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguia, vetia ul Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, heliothis virescens, ze ), Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta marinade Lass (Hyponomeuta malinellus), Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella,

  Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Limantria disparna, Limantria disparna・ Lyonetia clerkella 、 Malacosoma neustria 、 Manestra brassicae 、 Orgyia pseudotsugata 、 Ostrinia nubilalis 、 ea ole (Pectinophora gossypiella), Peridroma saucia, Phalera bucephala, Phthhorimaea operculera (Phthorimaea opercul) ella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Pseudoplusia includens, Pseudoplusia includens Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, pod ), Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis;

  Coleoptera (Insecta), eg Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, dis Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Brucus rufimanus Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma Trifrucata ma trifurcata), Ceutorrhynchus assimilis, Ceutorrhynchus napi, Caetocnema tibialis, rot, Giodes rio ), Diabrotica longicornis, Diabrotica-12-punctata, Diabrotica virgifera, Epilachna varivestis, Etrixach hirtipis E Eutinobothrus brasiliensis), Hyrobius abietis,

  Hipera brunneipennis, Hipera postica, Lips typographus, Lema bilineata, Lema melanopus, Leptitarsa decemline inta・ Limonius californicus, Risorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melontha hipolo, Mellontha hippolo Oulema oryzae, Ortiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae , Pyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Pyllotre neolus (Phyllotreta nemorras) Sitona lineatus and Sitophilus granaria;

  Diptera (Diptera), such as Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitaiana bee , Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, acus cupi, acus cupi Dacus oleae, Dasineura brassicae, Fanni canicularis, Gasterophilus intestinalis, Tsetse fly (Glossina morsitans), Haematobia irritans, Haplodiprossis equestri (Haplodiplosis equestris), Hylemyia platura, Hippoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia cuprina, Lucilia caprina (Lucilia sericata), Lycoria pectoralis, wheat fly (Mayetiola destructor), housefly (Musca domestica), housefly (Muscina stabulans), sheep fly (Oestrus ovis), Oscine ella frit (Oscine ella frit) Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Phagoretis pomonera (Rhagolet) is pomonella, Ab (Tabanus bovinus), Tipula oleracea and Tipula paludosa;

Thrips, such as Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, E (Thrips oryzae), Southern thrips (Thrips palmi), and Thrips tabaci;
Hymenoptera (Hymenoptera) such as Atthalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa mineste testudinea), Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta;

  Heterogenes (Hemiptera), such as Acrosternum hilare, Blisssus leucopterus, Cyrtopertis notatus, Dysdercus cingulatus, Dysdercus cingulatus, Dysdercus cingulatus intermedius, Eurygaster integriceps, Euschistus impictiventri, Leptoglossus phyllopus, Lygus lineolaris, L. Nezara viridula), Piesma quadrata, Solubea insularis and Thyanta perditor;

  Homozoans (Homoptera), for example, Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Strawberry aphids (Aphisbes) , Aphis pomi, Aphis gossypi, Aphis grossulariae, Aphis schneideri, Aphis spiraecola, Aphis ramae (Acyrthosiphon pisum), Potato beetle aphid (Aulacorthum solani), Brachycaudus cardui, Brachycaudus helichrysi, Brachycaudus persicae (Brachycaudus persicae) Brachycaudus prunicola, Brevicoryne brassicae, Capitophorus horni, Cerosipha gossypii, Chaetosiphon fragaefolii, zu rib, sri Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, dysaphisy, diasaphis Fabae (Empoasca fabae), peach beetle (Hyalopterus pruni), tyshamidria aphid (Hyperomyzus lactucae),

  Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Maranaphis pyrarius, pol Meumorum Red aphids (Myzus persicae), Japanese aphids (Myzus ascalonicus), Japanese aphid aphids (Myzus cerasi), Hanzu vultures (Myzus varians), Nasonovia ribis-nigri, gen Nila pari ), Pemphigus bursarius, Perkinsiella saccharicida, Hophoron humuli, Psylla mali, Psylla piri, Lo Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Rhopalosiphum padi, Rhopalosiphum insertum, Sappaphis mala (Sappaphis mala) Aphids (Schizaphis graminum), Schizoneura lanuginosa, Sitobion avenae, Trialeurodes vaporariorum, Toxoptera aurantiiand, and oli

  Isopods (Isoptera), for example, Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus and Termes natalensis;

  Species (Orthoptera), for example, Acheta domestica, Blattella orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllota Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Melanoplus spretus Nomadacris septemfasciata, cockroach (Periplaneta americana), Sistocerca americana, Sistocerca peregrina, Stauronotas ma Canas (Stauronotus maroccanus) and Kurazumiuma (Tachycines asynamorus);

  Spiders, eg spiders (Acari), eg, Acarididae, Tickidae and Amanidae, eg, Amblyomma americanum, Amblyomma variegatum, Argas persicus, Middle wall mite (Boophilus annulatus), Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Hyalomma truncatum, Ixodes ricinus, undus und Ornithodorus moubata, Otobius megnini, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus appendiculatus , Rhipicephalus evertsi, Sarcoptes scabiei, and wheat spider mite spp. (Eriophyidae spp.), For example, apple rustles (Aculus schlechtendali), Phyllocoptrata olerios (Phyllocoptrata oleio es Mites (Tarsonemidae spp.), For example Phytonemus pallidus and Polyphagotarsonemus latus; Mites, Tenuipalpidae spp. Nite spider mite (Tetranychus cinnabarinu), Kanzawa spider mite (Tetranychus kanzawai), Tetranicus pacificus (Tetranychus pacificus), Spider mite (Tetranychus telarius), Nite spider mite (Tetranychus urticae), Apple spider mite (Panonychus ul) i), Panonychus citri, and oligonychus pratensis; and

  Nematodes, such as plant parasitic nematodes and nematodes present in soil. Plant parasitic nematodes include, for example, root-knot nematodes, Meloidogyne hapla, sweet potato root-knot nematodes (Meloidogyne incognita), and other root-knot nematodes (Meloidogyne javanica); Globodera rostochiensis and other Globodera species; Heterodera avenae, soybean cyst nematode (Heterodera glycines), cyst nematode (Heterodera schachtii), clover cyst nematode (Heterodera trifolii) and other species Seed gall nematodes, Anguina species; Stem and leaf nematodes, Aphelenchoides species; Sting nematodes, Veronoramus longicauuda (Belonolaimus longicaudatus) and other Belonolaimus species; Pine nematodes, Pine nematodes (Bursaphelenchus xylophilus), and other nematodes (Bursaphelenchus species); Ring nematodes (Ring nematodes, Ring nematodes species, Criconemella species, Criconemoides species, Mesocriconema species; Stem and bulb nematodes, Ditylenchus destructor, Ditylenchus and other diplenci Ditylenchus species; Awl Nematoda, Dolichodorus species; Spiral nematodes, Heliocotylenchus multicinctus and other Heliocotylencus Species; sheath and nematode Nematoda, Hemicycliophora species and Hemicriconemoides species; Hirshmanniella species;

  Lance nematodes, Hoploaimus species; false rootknot nematodes, Nacobbus species; Needle nematodes, Longidorus elongatus and other Nagari Longidorus species; Pin nematodes, Paratylenchus species; Lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans, Negus (Pratylenchus curvitatus), Platilencus goodey and other Pratylenchus species; Burrowing nematodes, Radopholus similis and other Radophus species; Radophus species; Reniform nematodes, Rotylenchus robustus, and other Rotylenchus species; Scutellonema species; Stubby root nematodes, Trichodoras primibas and other tivi Trichodorus species, Paratrichodorus species; Stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, and other Tylenchorhynchus dubius species species); Citrus nematodes, Tylenchulus species; Dagger nematodes, Xiphinema species; and other plant-parasitic Nematoda species.

  Compounds of formula I or II and compositions comprising them may also be useful for molluscs, particularly against slugs. Molluscs that can be controlled by the methods and compositions of the present invention are preferably molluscs, including gastropods, more preferably pulmonary omentum, even more preferably snails and slugs, and most preferably Include, for example: Ampullariidae; Arion (A. ater, A. circumscriptus, A. hortensis), A. rufus); Bradybaenidae (Bradybaena fruticum); Cepaea (C. hortensis, C. Nemoralis); ochlodin); Deroceras (D. agrestis, D. empiricorum, D. laeve, D. reticulatum); cus) (D. rotundatus); Eunomphalia; Galba (G. trunculata; Helicelia (H. itala), H. obbia (H. obvia)); Helicidae (Helicigona arbustorum); Helicodiscus; Helix (H. aperta); Remax (L. Cineleoniger) (L. cinereoniger), L. flavus, L. marginatus, L. maximus, L. tenellus); Limnaea; Milax ( Milax (M. gagates, M. marginatus, M. sowerbyi); Opeas; Pomacea (P. canaticulata) ; Valonia and Zanitoide (Zanitoides). The combination according to the invention is particularly effective against Deroceras, for example Deroceras reticulatum.

  Compounds of formula I or II and compositions comprising them are particularly suitable for the control of insects and / or nematodes. Furthermore, the compounds of formula I (especially those compounds disclosed in Tables 1.1-1.49) or the compounds of formula II (especially those compounds disclosed in Tables 2.1-2.13) and compositions comprising them are It is particularly suitable for the control of pests selected from the order Lepidoptera, Lepidoptera, Diptera, Common moths and / or nematode nets.

  In a preferred embodiment of the invention, the compounds of formula I (for example those compounds disclosed in Table 1.1-1.49) or the compounds of formula II (especially those compounds disclosed in Table 2.1-2.13) and These compositions can be used for the control of insects or arachnids, in particular lepidoptera, common lepidoptera, coleoptera and / or dipterans, and mite arachnids.

The compounds of formula I of the present invention (eg those compounds disclosed in Table 1.1-1.49) or the compounds of formula II (eg those compounds disclosed in Table 2.1-2.13), and compositions thereof are Spiders of order, Coleoptera, Common order, Homogeneous, and Mite, such as Heliothis spp. (Heliothis spp.), Slip spp. (Thrips spp.), Diabrotica spp. (Diabrotica spp.), Misuzu To control insects of spp. (Myzus spp.), Aphis spp. (Aphis spp.), Spodoptera spp. (Spodoptera spp.), Plutella spp. (Plutella spp.), and Tetranychidae spp. Is particularly useful.
For use in the method of the invention, the compounds of formula I or II can be converted into conventional formulations, such as solutions, emulsions, suspensions, dusts, powders, pastes, granules and solutions that can be sprayed directly. The use form depends on the particular purpose and application method. The formulation and application methods are chosen in each case to ensure an even distribution of the compounds of the formula I according to the invention.

  Formulations combine the compounds of the present invention with conventional formulation aids suitable for formulating agrochemicals, such as solvents and / or carriers, optionally emulsifiers, surfactants and dispersants, preservatives, antifoam agents, -For coagulant, seed treatment formulations, also prepared by known means, optionally by spreading with colorants and / or binders and / or gelling agents (for example, for reconsideration, American Patent 3,060,084, EP-A 707 445 (for liquid concentrate), Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill , New York, 1963, pages 8-57 and et seq.WO 91/13546, U.S. Patent No. 4,172,714, U.S. Patent No. 4,144,050, U.S. Patent No. 3,920,442, U.S. Patent No. 5,180,587, U.S. Patent No. 5,232,701, US Patent 5,208,030, GB 2,095,558, US Patent 3,299,5 66, Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989 and Mollet, H., Grubemann, A., Formulation technology, Wiley VCH Verlag GmbH, Weinheim (Germany), 2001, 2.DA Knowles, Chemistry and Technology of Agrochemical Formulations, Kluwer Academic Publishers, Dordrecht, 1998 (ISBN 0-7514-0443-8) See

Suitable solvents / carriers are for example:
-Solvents such as aromatic solvents (eg Solvesso products, xylene and the like), paraffins (eg mineral fractions, alcohols (eg methanol, butanol, pentanol, benzyl alcohol), ketones (eg cycloxanone, γ -Butyrolactone), pyrrolidone (N-methyl-pyrrolidone (NMP), N-octylpyrrolidone (NOP)), acetate (glycol diacetate), alkyl lactate, lactones such as g-butyrolactone, glycol, fatty acid dimethylamide, fatty acid and Fatty esters, triglycerides, oils of vegetable or animal origin and modified oils, such as alkylated peanut oils In principle, solvent mixtures can also be used.

-Carriers such as ground natural minerals and ground synthetic minerals such as silica gel, finely divided silicic acid, silicates, talc, kaolin, attaclay, coal stone, lime, chalk, wood, ocher, clay, bitterness Apatite, diatomaceous earth, calcium sulfate and magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea and products of plant origin such as cereal foods, tree bark food, wood flour and nuts Shell food, cellulose powder and other solid carriers.
Suitable emulsifiers are nonionic and anionic emulsifiers such as polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates.
Examples of dispersants are lignin-sulfite pulp liquor and methylcellulose.

  Suitable surfactants include lignosulfonic acid, naphthalene sulfonic acid, phenol sulfonic acid, alkali metal, alkaline earth metal and ammonium salts of dibutyl naphthalene sulfonic acid, alkyl aryl sulfonate, alkyl sulfate, alkyl sulfonate, fatty alcohol sulfate. , Fatty acids and sulfated fatty alcohol ethers, sulfonated naphthalene and naphthalene derivatives and formaldehyde condensates, naphthalene or naphthalenesulfonic acid and phenol and formaldehyde condensates, polyoxyethylene octylphenyl ether, ethoxylated Isooctylphenol, octylphenol, nonylphenol, alkylphenyl polyglycol ether, tributylphenyl poly Glycol ether, tristearyl phenyl polyglycol ether, alkylaryl polyether alcohol, alcohol and fatty alcohol / ethylene oxide condensate, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, lauryl alcohol poly Glycol ether acetal and sorbitol ester.

In addition, anti-freezing agents such as glycerin, ethylene glycol, propylene glycol and bactericides can be added to the formulation.
Suitable antifoaming agents are for example antifoaming agents based on silicon or magnesium stearate.
Suitable preservatives are, for example, dichlorophen and benzyl alcohol hemiformal.

  Suitable thickeners are compounds that impart a pseudoplastic flow behavior to the formulation, i.e. a low viscosity in the shaking stage. For example, commercially available thickeners based on polysaccharides such as Xanthan Gum ™ (Kelzan ™ from Kelco), Rhodopol ™ 23 (Rhone Poulenc) or Veegum ™ (from RT. Vanderbilt), Or, organic phyllosilicates such as Attaclay ™ (from Engelhardt) may be mentioned herein.

  Suitable antifoaming agents for the dispersions according to the invention are, for example, silicone emulsions (eg Silicon ™ SRE from Rhodia, Wacker or Rhodorsil ™), long chain alcohols, fatty acids, organic fluorine compounds and mixtures thereof. It is. Biocides can be added to stabilize the compositions of the invention against attack by microorganisms.

  Suitable biocides are commercially available, for example, as isothiazolones such as commercial products, Proxel (TM) from Avecia (or Arch) or Acticide (TM) RS from Thor Chemie and Kathon (TM) MK from Rohm and Haas. Based on the compound that is present.

  Suitable antifreeze agents are organic polyols such as ethylene glycol, propylene glycol or glycerol. They are usually used in an amount of not more than 10% by weight, based on the total weight of active compounds.

  Where appropriate, the active compound compositions according to the invention comprise 1 to 5% by weight of buffer, based on the total amount of the formulation prepared, in order to adjust the pH, and the buffer used. The amount and type of liquid depends on the chemical nature of the active compound. Examples of buffers are alkali metal salts of weak inorganic or organic acids such as phosphoric acid, nitric acid, acetic acid, propionic acid, citric acid, fumaric acid, tartaric acid, oxalic acid and succinic acid.

  Suitable materials for the preparation of solutions, emulsions, pastes or oil dispersions that can be sprayed directly are medium to high boiling mineral oil fractions such as kerosene or diesel oil, as well as coal tar oil and oil of vegetable or animal origin. Aliphatic cyclic and aromatic hydrocarbons such as toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalene or derivatives thereof, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strong polar solvents such as Dimethyl sulfoxide, N-methylpyrrolidone and water.

  Powders, spreading materials and dusts can be prepared by mixing the active substances with a solid carrier or by simultaneous grinding.

  Granules, such as coated granules, implemented granules and homogeneous granules, can be prepared by combining the active ingredient with a solid carrier. Examples of solid carriers are mineral earth such as silica gel, silicate, talc, kaolin, attaclay, coal stone, lime, chalk, wood, ocher, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground Synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, nitric acid, ammonium, urea, and products of plant origin such as cereal food, tree bark food, nutshell food, cellulose powder and other solid carriers.

In general, the formulations comprise 0.01 to 95% by weight of active ingredient, preferably 0.1 to 90%. The active ingredient is used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
For seed treatment purposes, each formulation is 2 to 10 times to lead to a concentration for easy use of 0.01 to 60% by weight, preferably 0.1 to 40% by weight of active compound preparation. Can be diluted.

  The compounds of the formula I or II can be used in the form of their formulations or use forms prepared therefrom, for example directly sprayable solutions, powder suspensions or dispersions, emulsions, oil dispersions, pastes, dust products, spreads Can be used by means of spraying, atomizing, dusting, spreading or pouring in the form of materials or granules. Their use depends entirely on the intended purpose; they are intended in each case to ensure the most optimal possible distribution of the active compounds.

  Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. In order to prepare emulsions, pastes or oil dispersions, the substances themselves or substances dissolved in oils or solvents can be homogenized in water by means of wetting agents, thickeners, dispersing agents or emulsifiers. On the other hand, it is possible to prepare concentrates composed of active substances, wetting agents, thickeners, dispersants or emulsifiers and, if possible, solvents or oils, and such concentrates are based on water. Suitable for dilution.

  The active ingredient concentration in ready-to-use products can vary within a relatively wide range. In general, they are 0.0001 to 10% by weight, preferably 0.01 to 1% by weight. The active ingredient is also conveniently used in the micro-process (ULV), allowing the application of formulations comprising more than 95% by weight of the active ingredient or the application of the active ingredient without additives.

The following are examples of formulations:
1. Product for dilution with water. For seed treatment purposes, such products can be applied to diluted seeds or undiluted seeds.

A) Water-soluble concentrate (SL, LS) :
10 parts by weight of the active compound are dissolved in 90 parts by weight of water or a water-soluble solvent. As an alternative, wetting agents or other auxiliaries are added. The active compound dissolves on dilution with water, thereby obtaining a formulation containing 10% (w / w) of active compound.

B) Dispersible concentrate (DC) :
20 parts by weight of active compound are dissolved in 70 parts by weight of cyclohexanone and 10 parts by weight of a dispersant, for example polyvinylpyrrolidone, are added. Dilution with water gives a dispersion, whereby a formulation containing 20% (w / w) of active compound is obtained.

C) Emulsifiable concentrate (EC) :
15 parts by weight of the active compound are dissolved in 7 parts by weight of xylene and calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight) are added. Dilution with water gives an emulsion, whereby a formulation with 15% (w / w) of active compound is obtained.

D) Emulsion (EW, EO, ES) :
25 parts by weight of the active compound are dissolved in 35 parts by weight of xylene and calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight) are added. This mixture is introduced into 30 parts by weight of water by means of an emulsifying machine (eg Ultraturrax) and a homogeneous emulsion is produced. Dilution with water gives an emulsion, whereby a formulation containing 25% (w / w) of active compound is obtained.

E) Suspension (SC, OD, FS) :
In a stirred ball mill, 20 parts by weight of the active compound are finely ground with 10 parts by weight of a dispersant, a wetting agent and 70 parts by weight of water or an organic solvent to obtain a fine suspension of the active compound. Dilution with water gives a stable suspension of the active compound, whereby a formulation with 20% (w / w) of active compound is obtained.

F) Water-dispersible granules and water-soluble granules (WG, SG) :
50 parts by weight of the active compound are finely ground with 50 parts by weight of a dispersant and a wetting agent and produced by means of technical equipment (eg extrusion, spray tower, fluidized bed) as water-dispersible water-soluble granules. Dilution with water gives a stable dispersion or solution of the active compound, whereby a formulation with 50% (w / w) of active compound is obtained.

G) Water-dispersible powder and water-soluble powder (WP, SP, SS, WS) :
75 parts by weight of active compound are ground together with 25 parts by weight of dispersant, wetting agent and silica gel in a rotor-starter mill. Dilution with water gives a stable dispersion or solution of the active compound, whereby a formulation with 75% (w / w) of active compound is obtained.

H) Gel-formulation (GF) :
In a stirred ball mill, 20 parts by weight of the active compound are finely pulverized with 10 parts by weight of a dispersant, 1 part by weight of a gelling agent wetting agent and 70 parts by weight of water or an organic solvent to suspend the finely divided active compound. Obtain a liquid. Dilution with water gives a stable suspension of the active compound, whereby a formulation with 20% (w / w) of active compound is obtained.

2. Product applied undiluted for foliar application. For seed treatment purposes, such products can be diluted or undiluted and applied to the seed.
I) Fine powder (DP, DS) :
5 parts by weight of active compound are ground finely and mixed homogeneously with 95 parts by weight of finely divided carillons. This gives a finely divided product with 5% (w / w) of active compound.

J) Granules (GR, FG, GG, MG) :
0.5 parts by weight of active compound is ground finely and combined with 95 parts by weight of carrier, thereby obtaining a formulation with 0.5% (w / w) of active compound. Current methods are extrusion, spray-drying or fluidized bed. This gives granules to be applied undiluted for foliar use.

K) UlV solution (UL) :
10 parts by weight of the active compound are dissolved in 90 parts by weight of an organic solvent, for example xylene. This gives a product with 10% (w / w) of active compound, which is applied undiluted for foliar use.

Accordingly, there is also provided herein a composition in the form of a formulation comprising a compound of formula I or II as defined in the first aspect and one or more conventional compounding inerts. This composition is particularly preferred for seed treatment.
Various types of oils, wetting agents, adjuvants, herbicides, fungicides, other insecticides or fungicides can be added to the compound, if appropriate, just prior to use (tank mixture). These agents are usually mixed with the agents of the present invention in a weight ratio of 1:10 to 10: 1.
In one embodiment, the compound of formula I and the compound of formula II can also be used as a mixture for pest control applications as described herein.

  The compounds of formula I or II and their compositions may contain other active ingredients such as other insecticides, insecticides, fungicides, herbicides, feeds such as ammonium nitrate, urea, potash and superphosphates, herbicides Can be applied with agents and plant growth regulators, safeners and nematicides. These additional ingredients are combined with the above active ingredients, either continuously or, where appropriate, simply added just before use (tank-mix) or supplied as a blended product (pre-mix) Can be used. For example, plants can be sprayed with a composition comprising a compound of Formula I or II before or after being treated with other active ingredients. In general, active ingredients, such as combinations of compounds of formula I or II, are used in seed treatment applications as tank-mix or pre-mix compositions.

  Individual additional active ingredients can be mixed with the compound of formula I or II in a weight ratio of 1:10 to 10: 1. In the case of a plurality of additional active ingredients and a compound of formula I or II, the weight ratio between any two active ingredients (including compounds of formula I or II) is 1:10 to 10: 1 obtain. The resulting composition often provides a wider insecticidal range of action.

  The following list of pesticides (M & F), together with which the compounds of formula I or II of the present invention can be used and a substantial synergistic effect that can be used is generated, illustrates possible combinations. Yes, without any restrictions:

  M.1. Organic (Thio) phosphates: Acephate, Azemethiphos, Azinphosmethyl, Chlorpyrifos, Chlorpyrifos-Chyl, Chlorfenvinphos, Diazinon, Dichlorvos, Dicrotophos, Dimethoate, Disulfotone, Ethion, Fenitrothion, Fentione, Isoxathion, Malathion, Methamide Phosphorus Methidathion, methylparathion, mevinphos, monocrotophos, oxydemetonmethyl, paraoxon, parathion, phentoate, hosalon, phosmet, phosphamidone, folate, foxime, pirimiphosmethyl, profenophos, prothiophos, salprophos, tetrachlorvinphos, terbufos, triazophos, trichlorfos;

  M.2. Carbamate: Alanicarb, Aldicarb, Bengiocarb, Benfuracarb, Carbaryl, Carbofuran, Carbosulfan, Phenixicarb, Furatiocarb, Methiocarb, Mesomil, Oxamyl, Pirimicarb, Propoxur, Thiodicarb, Triazamate;

  M.3. Pyrethroid: Aresulin, Bifenthrin, Cyfluthrin, Cyhalothrin, Cifenothrin, Cypermethrin, α-Cypermethrin, β-Cypermethrin, ζ-Cypermethrin, Deltamethrin, Empensrin, Esfenvalerate, Etofen Proxy, Fenpropathrin, Fenvalate, imiprosulin, λ-cyhalothrin, permethrin, prareslin, pyrethrins I and II, resmethrin, silafluophene, τ-fulvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, profluthrin, dimefrin

  M.4. Growth regulator: a) Chitin synthesis inhibitor: Benzoylurea: Chlorfluazuron, Diflubenzuron, Flucyclouron, Fluphenoxyuron, Hexaflumuron, Lufenuron, Novallon, Teflubenzuron, Triflumuron; Buprofezin, Geophenolone, Hexitazox, B) ecdysone antagonists: halofenozide, methoxyphenozide, tebufenozide, azadirachtin; c) juvenoids: pyriproxyfen, metoprene, phenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, spirotetramate ;

M.5. Nicotinic receptor agonist / antagonist compounds: clothianidin, dinotefuran, imidacloprid, thiomethoxam, nitenpyran, acetamiprid, thiacloprid and AKD-1022;
M.6. GABA antagonist compound: acetoprole, endosulfan, epiprole, fipronil, vanilliprole, pyrafluprole, pyriprole, the following formula I ² :

A phenylpyrazole compound represented by:
M.7. Macrocyclic craton insecticides: Abamectin, Emamectin, Milbemectin, Lepimectin, Spinosad;
M.8. METI I compounds: phenazaquin, pyridaben, tebufenpyrad, tolfenpyrad, flufenerim;

M.9. METI II and III compounds: acequinosyl, fluacyprim, hydramethylnon;
M.10. Uncoupler compound: chlorfenapyr;
M.11. Oxidation phosphorylation inhibitor compounds: cyhexatin, diafenthiuron, fenbutane oxide, propargite;
M.12. Molting agent: cyromazine;
M.13. Mixed functional oxidase inhibitor compounds; piperonyl; piperonyl butoxide;

M.14. Sodium channel blocker compounds: indoxacarb, metaflumizone;
M.15. Various: Amitraz, Benclothiaz, Bifenazata, Cartap, Flonicamid, Pyridalyl, Pymetrozine, Sulfur, Thiocyclam, Flubendiamide, Sienopyrafen, Flupyrazophos, Sflumetofene, Amidoflumet, Pyrifluquinazone, Formula I ³ below

Aminoquinazolinone compound represented by the formula: N-R'-2,2-dihydro-1-R "cyclo-propanecarboxamide-2- (2,6-dichloro-α, α, α-tri-fluoro-p-tolyl ) Hydrazone or N-R'-2,2-di (R ^l ") propionamido-2- (2,6-dichloro-α, α, α-trifluoro-p-tolyl) -hydrazone, where R ' Is methyl or ethyl, halo is chloro or bromo, R ″ is hydrogen or methyl, and R ′ ″ is methyl or ethyl;
Anthranilamide compounds as chlorantraniliprole or the following formula I ⁴ :

JP 2002 284608, WO 02/89579, WO 02/90320, WO 02/90321, WO 04/06677, WO 04/20399, JP 2004 99597, WO 05/68423 No., malononitrile compounds as described in WO 05/68432) or (WO No. 05/63694, in particular malononitrile compound _{CF 3 (CH2) 2C (CN} ) 2CH2 (CF2) 3CF 2 H, CF 3 (CH2) 2C (CN) 2CH2 (CF2) 5CF ₂ H, CF ₃ (CH2) 2C (CN) 2 (CH2) 2C (CF ₃ ) 2F, CF ₃ (CH2) 2C (CN) 2 (CH2) 2 (CF ₂ ) 3CF3, CF2H (CF2 ) 3CH2C (CN) 2CH2 (CF2) 3CF ₂ H, CF ₃ (CH2) 2C (CN) 2CH2 (CF2) ₃ CF3, CF ₃ (CF ₂ ) 2CH2C (CN) 2CH2 (CF2) ₃ CF ₂ H, and CF ₃ CF ₂ CH ₂ C (CN) ₂ CH ₂ (CF ₂ ) ₃ CF ₂ H; and the following formula I ⁵ as described in WO07 / 101601:

A compound represented by
Commercially available compounds of the group M, among other ^{publications, The Pesticide Manual, 13 th Edition} , may be found in British Crop Protection Council (2003).

Compounds and their preparation of the formula I ² is described in JP WO98 / 98/28279. Lepimectin is known from Agro Project, PJB Publications Ltd, November 2004. Benclothiaza and its preparation are described in EP-A145462. Methidathion and paraoxon and their preparation are described in Farm Chemicals Handbook, Volume 88, Meister Publishing Company, 2001. Acetoprole and its preparation are described in WO 98/28277. Metaflumizone and its preparation are described in EP-A1462456. Flupyrazophos is described in Pesticide Science 54, 1988, p.237-243 and US 4822779. Pyrafluprolol and its preparation are described in JP 2002193709 and WO 01/00614. Pyriprolol and its preparation are described in WO 98/45274 and US 6335357.

Amidoflumet and its preparation are described in US Pat. No. 6,221,890 and JP 21010907. Flufenelim and its preparation are described in WO 03/007717 word y and WO 03/007718. Siflumethofen and its preparation are described in WO 04/080180. Aminoquinazolinone compound of formula I ³ can fall is described in JP EP A1097932.

Anthranilamides as one of formula I ⁴ or as chloranthraniliprole and their preparation are described in WO 01/70671; WO 02/48137; WO 03/24222, WO 03/15518, WO 04 / 67528; WO 04/33468; and WO 05/1 18552. Macronitrile compound CF3 (CH2) 2C (CN) 2CH2 (CF2) 3CF2H, F3 (CH2) 2C (CN) 2CH2 (CF2) 5CF ₂ H, CF ₃ (CH2) 2C (CN) 2 (CH2) 2C (CF ₃ ) 2F, F ₃ (CH2) 2C (CN) 2 (CH2) 2 (CF ₂ ) 3CF3, CF2H (CF2) 3CH2C (CN) 2CH2 (CF2) 3CF ₂ H, F ₃ (CH2) 2C (CN) 2CH2 ( _{CF2) 3 CF3, CF 3 (} CF2) 2CH2C (CN) 2CH2 (CF2) 3CF 2 H, and _{F 3 CF2CH2C (CN) 2CH2 (} CF2) 3CF 2 H are described in JP WO05 / 63 694.

The mold killing partners are those partners selected from Group F consisting of:
F. 1 Acylalanine, for example benalaxyl, metalaxyl, oflase, oxadixyl:
F. 2 amine derivatives such as aldimorph, dodine, dodemorph, fenpropimorph, phenpropidin, guazatine, imineoctazine, spiroxamine, tridemorph;

F. 3 anilinopyrimidines such as pyrimethanil, mepanipyrim or sirodinyl;
F. 4 antibiotics such as cycloheximide, griseofulvin, kasugamycin, natamycin, polyoxin or streptomycin;
F. 5 azoles, e.g. bitertanol, Bro Mokona, cyproconazole, difenoconazole, dinitro Kona tetrazole, epoxiconazole, fenbuconazole, Furukikonazoru, flusilazole, hexaconazole, imazalil, metconazole, myclobutanil l, penconazole, pro Piconazole, prochloraza z, prothioconazole, tebuconazole, triadimethone, triadimenol, triflumizole, triticonazole, flutriahol;

F. 6 dicarboximide, such as iprodione, microzoline, procymidone, vinclozolin;
F. 7 dithiocarbamates, such as farbam, nabam, maneb, manokozeb, metham, methylam, propineb, polycarbamate, thiram, ziram, dineb;

F. 8 Heterocyclic compounds such as anilazine, benomyl, boscalid, carbendazim, carboxin, oxycarboxyl, cyazofamide, dazomet, dithianone, famoxadone, fenamidone, fenarimol, fuberidazole, flutolanil, furametopir, isoprothiolane, mepronil, probenazole , Proquinazide, pyriphenoxy, pinoquinolone, quinoxifene, sylthiofam, thiabendazole, tifluzamide, thiophanate methyl, thiazinyl, tricyclazole, trifolin;

F. 9 Copper fungicides such as Bordeaux mixture, copper acetate, basic copper chloride, basic copper sulfate;
F. 10 Nitrophenyl derivatives such as binapacryl, dinocup, dinobutone, nitrophthalisopropyl;
F. 11 phenylpyrrole, eg fenpiclonyl or fludioxonil
F. 12 strobilurin, such as azoxystrobin, dimoxystrobin, fluoxastrobin, cresoxime-methyl, metminostrobin, orisatrobin, picoxystrobin or trifloxystrobin;

F. 13 sulfenic acid derivatives, such as captafoy, captan, dithiofiuania foipette, trifluanid
F. 14 cinnemamide and analogs such as dimethonel, flumetovel or sulmorpho;
F. 15 Sulfur and other fungicides such as acibenzolar-S-methyl, benchavaricarb, carpropamide, chlorothalonil, cyflufenamide, simoxanyl, dazomet, diclomedin, diclocimet, dietofencarb, edifenphos, ethaboxam, fenhexamide, fentinamide Acetate, phenoxanyl, ferrimzone, fludinam, focetyl, focetyl-aluminum, iprovaricarb, hexachlorobenzene, metolaphenone, pencyclon, propamoclub, phthalide, trocrophos-methyl, quintozene, zoxamide.

In a preferred embodiment, the invention also relates to a composition in the form of a formulation comprising a compound of formula I or II as defined above and one or more general formulation aids.
Accordingly, a compound of formula I or II as defined in the first aspect, and one or more active ingredients such as other insecticides (as described in the above list M and / or F), Insecticides, fungicides, herbicides, fertilizers such as ammonium nitrate, urea, potash and superphosphate, phytotoxic and growth regulators, safeners and nematicides, and optionally one or more Compositions comprising conventional formulated inerts are also provided herein; seed treatment compositions are particularly preferred.

In another aspect, the invention also comprises a compound of formula I or II as defined above and one or more active ingredients, and optionally one or more general formulating aids. It also relates to the composition in the form of a formulation.
Animal pests, i.e. insects, spiders and nematodes, plants, seeds, soil or water (where the plants grow) are known in the art with the present compounds of formula I or II or compositions thereof It can be contacted by any application method.

  A compound of formula I or II or an insecticidal composition thereof is produced by contacting a plant / crop with an insecticidally effective amount of a compound of formula I or II, in particular an animal pest, in particular an insect, acarid or spider form It can be used to protect plants and crops growing from attack or contamination. The active ingredients according to the invention are in particular on plants, in particular on agriculturally, horticulturally and forestally useful plants and decorative plants, or on such food organs such as fruits, flowers, leaves, stems. To control pests of the above type that occur on tubers, seeds or roots, and in many cases even on plant organs that are formed at later points, while remaining protected against those pests, i.e. Can be used to contain or destroy. The term “crop” refers to both growing and harvested crops.

  Suitable target crops are in particular: cereals such as wheat, barley, rye, oats, rice, corn (forage corn and sugar corn / sweet and field corn), or corn; beet such as sugar or Forage beet; fruits such as pomegranate, drupe or small fruit such as apples, pears, plums, peaches, bananas, almonds, cherries or berries such as strawberries, raspberries or blackberries; legumes such as beans, lentils, peas Bean or soybean; oil crops such as rape seed, mustard, poppy, olive, sunflower, coconut, castor, cocoa or groundnut; cucurbitaceae such as pumpkin, cucumber or melon; fiber food such as cotton, hemp, cannabis or burlap; Citrus fruits such as orange, lemon, green Rape fruit or mandarin; vegetables such as spinach, lettuce, asparagus, cabbage, ice bag, carrot, onion, tomato, potato or bell pepper; cucumber, such as avocado, cinnamon, camphor; and also tobacco, nuts, coffee, eggplant, Sugar cane, tea, pepper, butterfly vine, hops, ceraceae, latex plants, lawn, turf, lintels, and ornaments, crested morning glory, geranium / tengussiai, sansikimire, and genus genus.

  Furthermore, the compounds of formula I or II are also useful for the treatment of seeds from plants that are resistant to the action of herbicides, fungicides or insecticides for propagation, including genetic engineering methods. is there.

  For example, as a result of conventional methods of breeding or genetic engineering, herbicides such as bromoxynil or various herbicides (eg HPPD inhibitors such as primsulfuron, prosulfuron and trisulfoxysulfuron, EPSPS (5-enol-pyrovir) -Crops made tolerant to (diquimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors). An example of a crop that has been rendered tolerant to imidazolinones, such as imazamoxy, by conventional methods of breeding (mutagenesis) is Clearfield ™ summer rape (canola). Examples of crops that have been rendered genetically resistant to herbicides or various herbicides include glyphosate- and glufosinate-resistant corn varieties marketed under the trade names RoundupReady ™ and LibertyLink ™ .

  Furthermore, the compounds of formula I or II can also be produced by conventional breeding methods and / or mutants, or plants and seeds having modified characteristics compared to existing foods that can be produced by recombinant methods. Can also be used for processing. For example, recombinant modification of crop plants to modify starch synthesized in plants (eg, WO 92/11376, WO 92/14827, WO 91/19806), or trans having a modified fatty acid composition There are many cases describing a transgenic crop plant (WO91 / 13972).

  Furthermore, animal pests can be controlled by contacting the target pest, its food supply, habitat, breeding ground or location with an insecticidally effective amount of a compound of formula I or II. Application can be carried out before or after infection by the pests of the site, growing crops or harvested crops.

  The compounds of the invention can also be applied preventively to places where pest development is expected. The compounds of formula I or II can also be used to protect plants growing from pest attack or infection by contacting the plant with an insecticidally effective amount of a compound of formula I or II. “Contact” means direct contact (pest and / or plant, typically applying the compound / composition directly to the seed, leaf, stem or root of the plant) and indirect contact (pest And / or apply the compound / composition to the plant location).

  “Place” means a habitat, reproductive ground, plant, seed, soil, region, material or environment in which a pest or parasite is growing or can grow.

  In general, an “insecticidally effective amount” refers to an observable effect on growth, such as necrosis, death, delay, prevention and removal, destruction, or on the other hand, the effect of reducing the generation and activity of the target organism. It means the amount of active ingredient required to achieve. The pesticidally effective amount will vary with the various compounds / compositions used in the present invention. The pesticidally effective amount of the composition will also vary according to general conditions such as the desired pesticidal effect and duration, climate, target species, location, mode of application, and the like. .

  In a further aspect, the present invention provides a compound of formula I or II as defined above, or a composition thereof, which is a pest, plant, seed, plant part and / or plant organ, and / or individual thereof. Seeds, plants, plant parts and / or growing plant organs within a time at a later point in time against pest damage or control pests in crop protection comprising applying to the environment Relates to a method for protecting.

  In another aspect, the present invention provides a pest control method comprising applying a compound of formula I or II as defined above to a pest, a protective material and / or its environment. On how to do. In a first aspect, the material is selected from raw materials such as wood, fabrics, flooring and building materials. In a second aspect, the pests are controlled against damage to stored goods. In a third aspect, the pests are controlled in the hygiene area, particularly in the protection of humans, livestock and productive livestock.

Compounds of formula I or II are effective both through contact (eg, through soil, grass, walls, bed nets, carpets, plant parts or animal parts) and feeding (feed or plant parts).
In one embodiment, the present invention provides a compound of formula I or II or a composition thereof as defined above, wherein the pest, plant, seed, plant part and / or plant organ, and / or individual thereof The present invention relates to a method for improving the yield of harvested plants comprising applying to the environment.

For use on ants, termites, yellow bees, flies, mosquitoes, crickets or cockroaches, the compounds of formula I are preferably used in bait compositions.
The bait can be a liquid, solid or semi-solid preparation (eg a gel). The solid bait can be formed into various shapes and shapes suitable for each application, such as granules, blocks, sticks, discs. The liquid bait can be filled into various devices to ensure proper application, such as open containers, spray devices, droplet sources or evaporation sources. Gels are based on aqueous or oily matrices and can be formulated to specific needs in terms of stickiness, moisture retention or aging characteristics.

  The bait used in the composition is a product that is attractive enough to induce its uptake by insects such as ants, termites, yellow bees, flies, mosquitoes, crickets, etc., or cockroaches. The attraction effect can be manipulated by using feeding stimulants or sex pheromones. Food stimulants are for example from animal and / or plant proteins (meat-, fish- or blood meal, insect parts, yolk), fats and oils of animal and / or plant origin, or mono-, oligo- or poly-organic Although selected from sugars, especially sucrose, lactose, fructose, dextrose, glucose, starch, pectin or molasses or dense, they are not exclusive. Fresh or disintegrated parts of fruits, food, plants, animals, insects or specific parts thereof can also act as ingestion stimulants. Sex pheromones are known to be more insect specific. Certain pheromones are described in the literature and are known to those skilled in the art.

  Formulations of compounds of formula I as aerosols (eg in spray cans), oil sprays or pump sprays are very suitable for control by non-professional users of pests, flies, fleas, ticks, mosquitoes or cockroaches is there. Aerosol recipes are preferably active compounds, solvents such as lower alcohols (eg methanol, ethanol, propanol, butanol), ketones (eg acetone, methyl ethyl ketone, paraffin hydrocarbons (eg kerosene) (about 50-250 ° C). Dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, aromatic hydrocarbons such as toluene, xylene, water, and auxiliary agents such as emulsifiers such as sorbitol monooleate, 3 to 7 moles of ethylene oxide. Oleyl ethoxylates, fatty alcohol ethoxylates, perfume oils such as essential oils, esters of medium fatty acids and lower alcohols, aromatic carbonyl compounds, where appropriate stabilizers such as sodium benzoate, amphoteric surfactants, lower Epoch De, triethyl orthoformate case, and necessary, propellants, for example, a propane, butane, nitrogen, compressed air, dimethyl ether, carbon dioxide, nitrous oxide, or mixtures of these gases.

  Oil spray formulations are different from aerosol recipes where no propellant is used. The compounds of formula I and their respective compositions are also used in mosquito and fumigation coils, smoke cartridges, evaporator plates or long-term evaporators, and also in smoke paper, firewood pads or other heat independent evaporator systems obtain.

  Methods of controlling infectious diseases transmitted by insects (eg, malaria, dengue and yellow fever, lymphatic filariasis and leishmaniasis) with compounds of formula I or II and their respective compositions also include huts and Treating the surface of the house, spraying it with air and impregnating it with curtains, tents, fabric products, bed nets, flies and the like. Insecticidal compositions for application to fibers, fabrics, knitted products, nonwovens, net materials or foils, and tarpaulins preferably comprise an insecticide, optionally a mixture comprising an anthelmintic and at least one binder. .

  Suitable anthelmintic agents are preferably: N, N-diethyl-meta-toluamide (DEET), N, N-diethylphenylacetamide (DEPA), 1- (3-cyclohexane-1-yl-carbonyl ) -2-methylpiperazine, (2-hydroxymethylcyclohexyl) acetic acid lactone, 2-ethyl-1,3-hexanediol, indalone, methylneodecanamide (MNDA), pyrethroids not used for insect control, for example {(+ /-)-3-allyl-2-methyl-4-oxocyclopent-2-(+)-enyl-(+)-trans-chrysanthemate (Esbiothrin), derived from or with plant extracts such as limonene Identical anthelmintic agents, eugenol, (+)-eucamarolol (1), (-)-i-epi-eucamarolol or plants such as spotted gum, pokeweed, Cymbopogan martini, lemongrass, citronella Crude plant extracts al.

  Suitable binders are, for example, vinyl esters of aliphatic acids (eg vinyl acetate and vinyl versatate), acrylic and methacrylic esters of alcohols such as butyl acrylate, 2-ethylhexyl acrylate and methyl acrylate, mono- and di- Selected from polymers and copolymers of ethylenically unsaturated hydrocarbons such as styrene, and aliphatic dienes such as prodiene.

  Curtain and bed net impregnation is generally performed by dipping the fiber material into an emulsion or dispersion of an insecticide or spraying them onto the net.

  The compounds and compositions of formula I or II are made of woody materials such as trees, board enclosures, sleepers, etc. and buildings such as homes, outdoor toilets, factories, structural materials, furniture, leather, textiles, vinyl products, electrical wires and Can be used to protect cables, etc. from ants and / or termites, and to control ants and termites that are harmful to crops or humans (when pests enter homes and public facilities) . The compound of formula I is not only applied to the surrounding soil surface or underfloor soil to protect the wood material, it also can be used for material products such as underfloor concrete, floor columns, beams, plywood, furniture, etc. It can be applied to the surface of wood products, such as particle boards, half boards, etc., and vinyl products, such as coated electrical wires, vinyl sheets, barrier materials, such as polystyrene foam. In the case of application to ants that are harmful to crops or humans, the ant control agents of the present invention are applied to the crop or surrounding soil, or directly to the nest or the like.

  Further areas of use of the compounds of the formula I or II and their compositions according to the invention are the protection of storage goods and storage, and the protection of raw materials such as wood, textiles, flooring or buildings, and also in the hygiene sector Protecting humans, livestock and productive livestock against the types of insects specifically mentioned.

  In the hygiene sector, the compounds of formula I or II and compositions thereof are ectoparasites such as ticks, rotifers, cypresses, mites, flies (biting and licking), parasitic fly larvae, lice, Active against hair lice, bird lice and fleas.

Examples of such parasites are:
In the order of Anoplurida: Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp. And Solenopotes spp. ;
In the order of the Mallophagida, Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Wellnekiella spp. (Werneckiella) spp.), Lepikentron spp., Damalina spp., Trichodectes spp. and Felicola spp.;

  Among the Diptera and Nematocerina and Brachycerina suborders, Aedes spp., Anopheles spp., Clex spp., Simulium spp. Simulium spp.), Eusimulium spp., Febotomas spp. (Phlebotomus spp.), Ruzomya spp., Cricoides spp., Chrysops spp. (Chrysops spp.) Hybomitra spp. (Hybomitra spp.), Atyrotus spp. (Atylotus spp.), Tabanas spp. (Tabanus spp.), Haematopota spp. (Haematopota spp.), Philipomia spp. (Philipomyia spp.), Brakara spp. (Braula spp.), Musca spp. (Musca spp.), Hydrotae spp. (Hydrotaea spp.), Stomoxys spp. (Stomoxys spp.), Haematobia spp. (Haematobia spp.), Morelia spp. (Morellia spp.), Fannia spp. (Fannia spp.), Glossina spp. Fora spp. (Calliphora spp.), Lucilia spp. (Lucilia spp.), Chrysomya spp. (Wohlfahrtia spp.), Sarcophaga spp. (Sarcophaga spp.), Oestras spp. (Oestrus spp.), Hippoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., And Melofagas spp. spp.);

In the order of Siphonapterida, Plax spp. (Pulex spp.), Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.
In the eyes of heteroopterida, Simex spp. (Cimex spp.), Triatoma spp., Rhodius spp. (Rhodnius spp.), Panstrongylus spp. (Panstrongylus spp.);

Among the cockroaches, Blata orientalis, Periplaneta americana, Blattelagermanica and Spella spp. (Supella spp.);
In the order of the mite subfamily and meta- and meso-stigmata, Argas spp. (Argas spp.), Ornithodorus spp., Otobius spp. (Otobius spp.), Ixodes spp (Ixodes spp.), Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyoma spp. Hyalomma spp.), Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternoma spp. And Valora spp. (Varroa spp.);

  Among the Actinedida (Prostigmata) and Astigmata (Astigmata), Acarapis spp., Cheyletiella spp. Ornithocheyletia spp.), Myobia spp. (Myobia spp.), Psorerbutespi spp. (Psorergatesspp.), Demodex spp. (Demodex spp.), Trombikura spp. (Trombicula spp.), Listrophorus spp. ), Acarus spp. (Acarus spp.), Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psolopus (Psoroptes spp.), Corioptes spp. (Chorioptes spp.), Otodectes spp. (Otodectes spp.), Sarcoptes spp. (Sarcoptes spp.), Notoedres spp. (Notoedres spp.), Kunemid Coptes s pp. (Knemidocoptes spp.), Cytodites spp. (Cytodites spp.) and Laminosioptes spp. (Laminosioptes spp.).

The compounds of formula I and their compositions are also suitable for protection against insect appearance in the case of materials such as wood, textiles, plastics, adhesives, coatings, paper and cards, leather, flooring and buildings. is there.
For application to place or nest dwell soil treatment, or pests, the amount of active ingredient, 0.0001 / 100 m ^2, preferably in the range of 0.001 to 20 g / 100 m ^2.
Typical application rates in the protection of materials are 0.01 to 1000 g of compound of formula I / m ² treated material, preferably 0.1 to 50 g / m ² .

Insecticide compositions for use in impregnating materials are typically 0.001-95 wt%, preferably 0.1-45 wt%, and more preferably 1-25 wt% of at least one anthelmintic and / or Contains pesticides.
For use in bait compositions, a typical content of active ingredient is 0.001 to 15% by weight, desirably 0.001 to 5% by weight of a compound of formula I or II.

For use in spray compositions, the active ingredient content is 0.001 to 80% by weight, preferably 0.01 to 50% by weight and most preferably 0.01 to 15% by weight.
For use in the treatment of crops, the active ingredient application rates of the present invention are from 0.1 g to 4000 g / ha, desirably from 25 to 600 g / ha, more desirably from 50 to 500 g / ha.

  The compounds of formula I or II are particularly useful for the protection of seed from soil pests and the protection of the resulting plant roots, shoots and leaves from soil pests and leaf insects. Protection of the plant roots and shoots obtained is preferred. More preferred is protection of the resulting plant shoots from piercing and blood sucking insects, where protection from aphids is most preferred.

  Accordingly, the present invention relates to seeds from insects, in particular soil insects, comprising contacting seeds before sowing and / or before germination with a compound of general formula I or II or a salt thereof. And methods for the protection of seedling roots, shoots and leaves from insects, especially soil and leaf insects. Particularly preferred is a method in which the roots, shoots and / or leaves of the plant are protected, most preferably a method in which the shoots of the plant are protected from aphids.

  The term seed refers to all kinds of seeds and plant propagation material such as complete seeds, seed fragments, soccer, cereals, corms, fruits, tubers, cereals, rhizomes, cuttings, cut shoots and the like (provided that In a preferred embodiment, it means complete seeds, including but not limited to them.

The invention also comprises seeds coated with or containing a compound of formula I or II.
The term “covered by and / or comprising” generally means that the active ingredient is predominantly present on the surface of the seed at the time of application, provided that a majority of the ingredient or A few parts can penetrate into the seed material, depending on the application method. When the seed is planted (again), it can absorb the active ingredient.

  Seed treatment includes suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed spreading, seed soaking and seed pelleting. Seed treatment application of compounds of formula I or II can be carried out in any known manner, for example before sowing or during sowing / planting of seeds, by spraying or by spraying.

Compositions that are particularly useful for seed treatment are, for example:
A Soluble concentrate (SL, LS) D Emulsion (EW, EO, ES)
E Suspension (SC, OD, FS)
F Water-dispersible granules and water-soluble granules (WG, SG)
G Water-dispersible powder and water-soluble powder (WP, SP, WS)
H Gel-Formulation (GF) I Dispersible powder (DP, DS)

  Conventional seed treatment formulations include, for example, fluid concentrate FS, solution LS, powder DS for dry treatment, water dispersible powder WS for slurry treatment, water soluble powder SS and emulsion ES and EC, and gel formulation Includes GF. These formulations can be applied to the seed diluted or undiluted. Application to the seed is carried out before sowing, directly on the seed or after pre-germination. It can also be applied during seed sowing.

  In a preferred embodiment, the FS formulation is used for seed treatment. Typically, the FS formulation comprises 1 to 800 g / l active ingredient, 1 to 200 g / l surfactant, 0 to 200 g / l antifreeze, 0 to 400 g / l binder, 0 to It comprises 200 g / l dye and up to 1 L of solvent, preferably water.

  Particularly preferred FS formulations of compounds of formula I for seed treatment are usually 0.1 to 80% by weight (1 to 800 g / l) active ingredient, 0.1 to 20% by weight (1 to 200 g / l) of at least one Surfactants, such as 0.05-5 wt% water and 0.5-15 wt% dispersant, up to 20 wt%, such as 5-20 wt% antifreeze, 0-15 wt%, such as 1-15 wt% % Dyes and / or pigments, 0 to 40% by weight, for example 1 to 40% by weight binder (sticking agent / adhesive), optionally up to 5% by weight, for example 0.1 to 5% by weight thickener. , Optionally 0.1-2% by weight antifoam, and optionally preservatives such as biocides, antioxidants or concomitant (in amounts of 0.01-1% by weight), and up to 100% by weight Comprising a filler / vehicle.

The seed treatment formulation may further comprise a binder and optionally a colorant.
Binders can be added after treatment to improve the adhesion of the active material onto the seed. Suitable binders are block copolymer EO / PO surfactants and also polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylate, polymethacrylate, polybrene, polyisobutylene, polystyrene, polyethyleneamine, polyethyleneamide, polyethyleneimine (Lupasol ™, Polymin) (Trademark)), polyethers, polyurethanes, polyvinyl acetates, tyroses, and copolymers derived from these polymers.

  Optionally, a colorant can also be included in the formulation. Suitable colorants or pigments for seed treatment formulations are Rhodamine B, CI Dye Red 112, CI Solvent Red 1, Dye Blue 15: 4, Dye Blue 15: 3, Dye Blue 15: 2, Dye Blue 15 : 1, Dye Blue 80, Dye Yellow 1, Dye Yellow 13, Dye Red 1 12, Dye Red 48: 2, Dye Red 48: 1, Dye Red 57: 1, Dye Red 53: 1, Dye Orange 43, Dye Orange 34, Dye Orange 5, Dye Green 36, Dye Green 7, Dye White 6, Dye Brown 25, Basic Purple 10, Basic Purple 49, Acid Red 51, Acid Red 52, Acid Red 14, Acid Blue 9, Acid Yellow 23, Basic Red 10, The basic red is 108.

An example of a gelling agent is carrageenan (Satiagel ™).
In seed treatment, the application rate of the compound of formula I or II is generally 0.1 g to 10 kg / 100 kg seed, preferably 1 g to 5 kg / 100 kg seed, more preferably 1 g to 1000 g / 100 kg seed, And especially 1 g to 200 g / 100 kg of seed.
Accordingly, the present invention also relates to a seed comprising (or treated with) a compound of formula I or II, as defined herein, or an agriculturally useful salt thereof. The amount of the compound of formula I or II or the agriculturally useful salt thereof is generally from 0.1 g to 10 kg / 100 kg seed, preferably from 1 g to 5 kg / 100 kg seed, in particular from 1 g to 1000 g / 100 kg seed. .

Thus, the material treated with the compound of formula I or II relates to any material, for example seed, wood, net.
In individual aspects and embodiments of the present invention, “consisting essentially of” and its utilization forms are preferred embodiments of “comprising” and its utilization forms, and “consisting of” and its utilization forms are: Preferred embodiments of “consisting essentially of” and its utilization forms.
The following examples are for illustrative purposes and do not limit the invention.

S1a) 2-Bromo-6-cyano-benzenesulfonyl chloride :
A solution of 0.37 g sodium nitrite in 3 ml water was added to 1 g 2-amino-3-bromo-benzonitrile (Synthetic Communications (1989), 19 (13-14), 2255-63) in 8 ml concentrated hydrochloric acid. To the solution at -5 ° C. The mixture is stirred at -5 ° C for 90 minutes. In a separate flask, a solution of 0.22 g of cupric chloride dihydrate in 14 ml of glacial acetic acid is saturated with sulfur dioxide and then cooled to -8 ° C. The mixture with the diazonium salt is then added dropwise at −8 ° C. to −3 ° C. and stirred for 2 hours. The reaction mixture is poured into ice-cooled water. Extract the aqueous layer three times with dichloromethane. The combined organic layers are dried over magnesium sulfate, filtered and concentrated under vacuum. The resulting residue is suspended in cyclohexane and filtered. The resulting residue is washed with cyclohexane and dried to give 1.2 g of 2-bromo-6-cyano-benzenesulfonyl chloride.
¹ H-NMR (CDCl ₃ , 400 MHz): 8.15 (d, 1 H), 7.96 (d, 1 H), 7.67 (t, 1 H) ppm.

S1b) 7-Bromo-1,1-dioxo-1H-1λ ⁶ -benzo [d] isothiazol-3-ylamine :
2.1 ml ammonia (7M) in methanol is added to a solution of 1.85 g 2-bromo-6-cyano-benzenesulfonyl chloride in 40 ml tetrahydrofuran at ambient temperature. The reaction mixture is stirred at ambient temperature for 16 hours. The mixture is then poured into water and extracted with ethyl acetate. The organic layer is washed with water, dried over sodium sulfate, filtered and concentrated. Chromatography of the residue with cyclohexane: ethyl acetate (1: 1) gave 730 mg of 7-bromo-1,1-dioxo-1H-1λ ⁶ -benzo [d] isothiazol-3-ylamine (P1.1). obtain.
¹ H-NMR (DMSO d ⁶ , 400 MHz): 9.00 (s, br, 2H), 8.09 (d, 1 H), 7.77 (d, 1 H), 7.70 (t, 1 H) ppm.

S2a) 7-Bromo-2-isopropyl-1,1-dioxo-1,2-dihydro-1λ ⁶ -benzo [d] isothiazole-3-ylideneamine :
70 mg isopropylamine is added to a solution of 150 mg 2-bromo-6-cyano-benzenesulfonyl chloride in 5 ml tetrahydrofuran at ambient temperature. After 16 hours of stirring at ambient temperature, the mixture is poured into water and extracted with ethyl acetate. The organic layer is washed with water, dried over sodium sulfate, filtered and concentrated. Chromatography of the residue with cyclohexane: ethyl acetate (2: 1) gave 99 mg of 7-bromo-2-isopropyl-1,1-dioxo-1,2-dihydro-1λ ⁶ -benzo [d] isothiazole-3. -Obtain ylideneamine (P2.1).
¹ H-NMR (DMSO d ⁶ , 400 MHz): 9.88 (s, 1 H), 8.40 (d, 1 H), 8.10 (d, 1 H), 7.85 (t, 1 H), 4.60 (m, 1 H), 1.53 (d, 6H).

S3a) 3-Amino-1,1-dioxo-1H-1λ ⁶ -benzo [d] isothiazole-7-carbonitrile :
30 mg of tetrakis (triphenylphosphine) palladium (O) was converted to 100 mg of 7-bromo-1,1-dioxo-1H-1λ ⁶ -benzo [d] isothiazol-3-ylamine and 30 mg of cyanide under an argon atmosphere. Add to the copper II solution. After stirring for 24 hours at 120 ° C., the mixture is poured into water and extracted with toluene. The organic phase is washed with 20% aqueous ammonia and water, dried over sodium sulphate and evaporated. Chromatography of the residue with cyclohexane: ethyl acetate (1: 1) gave 22 mg of 3-amino-1,1-dioxo-1H-1λ ⁶ -benzo [d] isothiazole-7-carbonitrile (P1.4) Get.
¹ H-NMR (DMSO d ⁶ , 400 MHz): 9.21 (s, br, 2H), 8.40 (d, 1 H), 8.27 (d, 1 H), 8.00 (t, 1 H) ppm.

S4a) 1,1-dioxo-7-phenyl-1H-1λ ⁶ -benzo [d] isothiazol-3-ylamine :
170 mg 7-bromo-1,1-dioxo-1H-1λ ⁶ -benzo [d] isothiazol-3-ylamine, 119 mg phenylboronic acid, 10 mg palladium-acetate, 21 mg 2-dicyclohexylphosphino-2 ', 6'-Dimethoxybiphenyl and 415 mg potassium phosphate are suspended in 5 ml toluene. The mixture is stirred at 100 ° C. for 16 hours under an argon atmosphere. The reaction mixture is poured into water and extracted with ethyl acetate. The organic phase is washed with water, dried over sodium sulphate and evaporated. Chromatography of the residue with cyclohexane: ethyl acetate (1: 1) gave 41 mg of 1,1-dioxo-7-phenyl-1H-1λ ⁶ -benzo [d] isothiazol-3-ylamine (P1.5). obtain.
¹ H-NMR (DMSO d ⁶ , 400 MHz): 9.00 (d, br, 2H), 8.20 (d, 1 H), 7.94-7.80 (m, 4H), 7.55-7.45 (m, 3H) ppm.

S5: (7-Fluoro-1,1-dioxo-1H-1λ ⁶ -benzo [d] isothiazol-3-yl) -methyl-amine (P1.15) :
Step 1: 3-Chloro-7-fluoro-1,2-benzisothiazole 1,1-dioxide :
Refluxing 3.02 g 7-fluoro-1,2-benzisothiazol-3 (2H) -one 1,1-dioxide (EP291851 A2 19881123), 1.64 ml thionyl chloride and catalytic amount of DMF in 13 ml dioxane. Heat for 45 hours under. The mixture is concentrated and the residue is crystallized under toluene. 2.5 g of crude solid is obtained.

Step 2: (7-Fluoro-1,1-dioxo-1H-1λ ⁶ -benzo [d] isothiazol-3-yl) -methyl-amine (P1.15) :
260 mg of crude 3-chloro-7-fluoro-1,2-benzisothiazole 1,1-dioxide obtained in Step 1 is dissolved in 8 ml of dioxane and 0.33 ml of triethylamine is added. Next, 0.91 ml of a solution of methylamine (41%) in water is introduced. After stirring for 1 hour at room temperature, the reaction mixture is poured into water. The aqueous phase is extracted twice with ethyl acetate. The combined organic phase is washed with water and brine and concentrated. Crystallization of the residue under diethyl ether yields 190 mg of (7-fluoro-1,1-dioxo-1H-1λ ⁶ -benzo [d] isothiazol-3-yl) -methyl-amine as a solid ( mp 231-232 ° C).

The following method is used for LC-MS analysis:
Method: The following HPLC gradient conditions (solution A: 0.1% formic acid in water / acetonitrile (9: 1) and solvent B: 0.1% formic acid in acetonitrile) (Waters Alliance 2795LC)

Time (min) A (%) B (%) Flow rate (ml / min)
0 90 10 1.7
2.5 0 100 1.7
2.8 0 100 1.7
2.9 90 10 1.7

Column type: Waters Atlantis dc18; column length: 20 mm; column inner diameter: 3 mml: particle size: 3 microns; temperature: 40 ° C.
Table P1: A list of compounds of the following formula, prepared and characterized. The compounds can be prepared as described above or by similar methods known in the literature.

  Table P2: A list of compounds of the following formula, prepared and characterized.

Biological example:
B1: Myzus persicae (Red Aphid) (mixed population, incense test):
Individual wells of 24-well microtiter plates are filled with 0.6 ml of 30% sucrose solution containing 12.5 ppm test compound. To produce an aroma, the wells are covered with stretched paraffin and infected with a mixed population of S. persicae. Six days after infection, the samples are examined for mortality (ingestion activity).
Compounds P1.2, P1.3, P1.6, P1.7, P1.8, P1.10, P2.1 and P2.2 conferred at least 80% control of S. persicae.

B2: Mizus persicae (Red Aphid) (mixed population, feeding / residual contact activity, prevention):
Sunflower leaf discs are placed on agar on a 24-well microtiter plate and sprayed with 200 ppm test solution. After drying, the leaf disk is infected by a mixed age oilworm population. After 6 days of incubation, the samples are examined for mortality and specific effects (eg phytotoxicity).
Compounds P1.1, P1.2, P1.3, P1.7, P1.8, P1.9, P1.11, P1.13, P1.14, P1.15, P1.16, and P2.2 Granted at least 80% control of Mizus persicae.

B3: Mizus persicae (Aphid) (mixed population, systemic / feeding activity, treatment):
Pea seedling roots infected by the mixed age oilworm population are placed directly into the 24 ppm test solution. After 6 days of incubation, samples are examined for mortality and specific effects on plants.
Compounds P1.1, P1.2, P1.3, P1.7, P1.8, P1.9, P1.10, P1.1 1, P1.12, P1.13, P1.14, P1.15, P1.16, P1.17, P1.18, P1.19, P1.20, P1.21 and P1.22 gave at least 80% control of S. persicae.

Claims (17)

Formula I or II below:

[Wherein W is CR ³ ;
X is CR ⁴ ;
Y is CR ⁵ ;
R ¹ and R ⁶ are independently of each other H, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, R ⁷ C (═O) or R ⁸ HNC. (= O), where C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, R ⁷ C (= O) or R ⁸ HNC (= O) The groups can be unsubstituted or carry one or more halogen atoms and / or independently of each other cyano, nitro, amino, OH, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkoxy, C1-C6-haloalkylthio, (C1- C6-alkoxy) carbonyl, (C1-C6-alkyl) amino, di- (C1-C6-alkyl) amino, C3-C8-cycloalkyl, C1-C6-alkylcarbonyloxy, arylcarbonyloxy 1, 2 or 3 groups, each selected from the group consisting of xyl and aryl, can be carried, wherein said aryl group is unsubstituted or can carry one or more halogen atoms. Can be and / or independently of one another, selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, cyano and nitro, 1, 2 or Can carry three substituents;
R ² is H;
R ³ , R ⁴ and R ⁵ are independently of each other H, halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, C2-C6-alkenyl, N- combined 4-7 membered N-containing heterocycle, C2-C6- ^{alkynyl, R 9 C (= O)} , it is a OD or aryl; where D is C1-C6- alkyl, C2-C6- alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, benzyl or aryl; the 4-7 membered heterocycle, in addition to the bonded N atom, is independently of each other C (= O), O 1, 2 or 3 heteroatoms and / or heteroatoms as ring members selected from S, N and can be substituted or unsubstituted or halogen, C1-C6- (halo ) May be substituted by 1 or 2 substituents substituted from alkyl and C1-C6- (halo) alkoxy; and the aryl, whenever mentioned, Independently of each other, it can be unsubstituted or carry one or more halogen atoms and / or independently of each other, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6- Can carry 1, 2 or 3 substituents selected from the group consisting of alkoxy and C1-C6-haloalkoxy;
R ⁷ is C1-C6-alkyl, C2-C6-alkenyl or C3-C8-cycloalkyl, where individual groups can be halogenated;
R ⁸ is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or phenyl, wherein the phenyl group is unsubstituted, can carry one or more halogen atoms, and / or Independently of each other, may carry 1, 2 or 3 substituents selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy. Can; and
R ⁹ is H or C1-C6-alkyl;
However, in Formula II, R ¹ is H and R ⁶ is as defined above; and in Formula I, (a) at least one of R ¹ and R ^{3 to} R ⁶ is hydrogen (B) R ³ or R ⁴ is in each case other than Cl when the remaining five groups of R ^{1 to} R ⁶ are hydrogen, and (c) (i) R ³ is methyl. (Ii) R ⁴ is other than Cl, (iii) R ⁵ is other than Cl, and (iv) when R ⁵ is methoxy, R ³ is not Cl and (i) to ( In the individual cases of iv), R ¹ is H, R ⁶ is MeC (═O), and the remaining groups of R ^{2 to} R ⁵ are hydrogen]
And / or a salt thereof. The compound of claim 1, wherein R ³ is C1-C4-alkyl. The compound according to claim 1, wherein any two of R ³ , R ⁴ and R ⁵ are H. The compound according to claim 1 or 3, wherein R ³ and R ⁴ are H. The compound according to any one of claims 1 to 4, wherein R ¹ is H. R ¹ is a C1-C6- alkyl, any one compound according to claims 1-5. R ⁶ is selected from H, C2-C6-alkynyl, R ⁷ C (═O), R ⁸ HNC (═O) and C1-C6-alkyl, wherein the C1-C6-alkyl group is cyano, C1 -C6-alkoxy, C3-C8-cycloalkyl or aryl may be substituted and the C2-C6-alkynyl, R ⁷ C (═O), R ⁸ HNC (═O) and C1-C6-alkyl groups are 1 Or the compound of any one of Claims 1-6 which can carry | support several halogen atoms. R ⁵ is halogen, C1-C6- alkyl or C1-C6- haloalkyl, any one compound according to claims 1-7.   A composition comprising a compound of formula I or II according to any one of claims 1 to 8 and one or more customary formulation aids.   A composition comprising a compound of formula I or II according to any one of claims 1 to 8, one or more active ingredients, and optionally one or more customary formulation aids.   A method for controlling pests in crop protection or protecting seeds, plants, plant parts and / or growing plant organs at a later point in time against pest damage, 9. A compound of formula I or II or a composition thereof according to any one of claims 1 to 8 is applied to pests, plants, seeds, plant parts and / or plant organs and / or their individual environments. A method comprising that.   A seed comprising a compound of formula I or II according to any one of claims 1-8.   9. A compound of formula I or II or a composition thereof according to any one of claims 1 to 8 is applied to pests, plants, seeds, plant parts and / or plant organs and / or their individual environments. A method for improving the yield of harvested plants comprising:   A method for controlling pests comprising applying a compound of formula I or II according to any one of claims 1 to 8 to pests, protective materials and / or their environment.   15. A method according to claim 14, wherein the material is selected from raw materials such as wood, textiles, flooring and building materials.   15. The method of claim 14, wherein the pest is controlled against damage to stored goods.   15. A method according to claim 14, wherein the pest is controlled in the hygiene area, in particular in the protection of humans, livestock and productive livestock.